- First Total Synthesis and Biological Potential of a Heptacyclopeptide of Plant Origin
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Synthesis of a natural glycine-rich heptacyclopeptide - mahafacyclin A (7) was accomplished by solution-phase technique of peptide synthesis via coupling of tetrapeptide unit Boc-L-Thr-L-Ile-L-Leu-Gly-OH with tripeptide unit L-Val-L-Phe-Gly-OMe followed b
- Dahiya, Rajiv,Singh, Sunil
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Read Online
- Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts
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Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6
- Seitz, Alexander,Wende, Raffael C.,Roesner, Emily,Niedek, Dominik,Topp, Christopher,Colgan, Avene C.,McGarrigle, Eoghan M.,Schreiner, Peter R.
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p. 3907 - 3922
(2021/03/09)
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- Pd-Catalyzed Site-Selective C(sp2)-H Olefination and Alkynylation of Phenylalanine Residues in Peptides
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Pd-catalyzed site-selective C(sp2)-H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C-H functionalization. This p
- Zheng, Yong,Song, Weibin
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supporting information
(2019/05/08)
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- Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs
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Curcumin (CUR) is a natural yellow pigment from turmeric with extensive bioactivities. However its relatively poor solubility limited its absorption and bioavailability. In this study, a novel series of CUR-peptide conjugates were designed and synthesized
- Zhang, Jiyun,Wen, Hongmei,Shen, Fei,Wang, Xinzhi,Shan, Chenxiao,Chai, Chuan,Liu, Jian,Li, Wei
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- Pd-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides: Synthesis of indoline-2-carboxylate-containing dipeptides
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A palladium-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino aci
- Zheng, Yong,Song, Weibin,Zhu, Yefu,Wei, Bole,Xuan, Lijiang
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supporting information
p. 2402 - 2405
(2018/04/12)
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- 9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis
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A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy-to-access 9-silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization.
- Aspin, Samuel J.,Taillemaud, Sylvain,Cyr, Patrick,Charette, André B.
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supporting information
p. 13833 - 13837
(2016/10/26)
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- SMALL MOLECULE MODULATORS OF PCSK9 AND METHODS OF USE THEREOF
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A compound of Formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or racemic mixture or stereoisomer thereof, and methods for preventing or treating an LDL-cholesterol-related disease or disorder using such compound(s), and kits and comp
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Paragraph 0513
(2016/02/22)
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- A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
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A novel tropylium-based coupling reagent has been developed to facilitate the synthesis of a series of esters, amides, lactones and peptides under mild reaction conditions. Remarkably, this reagent can be used in catalytic amounts in conjunction with a sacrificial reagent, offering a new and efficient method for nucleophilic coupling reactions of carboxylic acids.
- Nguyen, Thanh V.,Lyons, Demelza J.M.
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supporting information
p. 3131 - 3134
(2015/06/17)
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- Diketo acids and their amino acid/dipeptidic analogues as promising scaffolds for the development of bacterial methionine aminopeptidase inhibitors
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Using diketoesters as the template, various derivatives were designed and the selected compounds were synthesized as bacterial methionine aminopeptidase (MetAP) inhibitors. The results of in vitro antibacterial screening revealed fifteen compounds (1a-c,
- Masood, Mir Mohammad,Pillalamarri, Vijay K.,Irfan, Mohammad,Aneja, Babita,Jairajpuri, Mohamad Aman,Zafaryab,Rizvi, M. Moshahid A.,Yadava, Umesh,Addlagatta, Anthony,Abid, Mohammad
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p. 34173 - 34183
(2015/04/27)
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- Direct modification of tripeptides using photoinduced decarboxylative radical reactions
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In order to explore the applicability of photoinduced electron transfer (PET) promoted decarboxylative reactions to the direct modification of peptides, a study was performed to assess the influence of amino acid side chains on photoreactions of N-terminal protected tripeptides. Photoinduced decarboxylation reactions of tripeptides, which are composed of central amino acids that possess alkyl, phenyl, thioether, hydroxy, and amide containing side chains, in the presence or absence of acrylonitrile and a thiol were found to proceed smoothly to give the corresponding radical addition, H-abstraction, and substitution products. Although photoreactions of tripeptides containing central amino acids with phenol and indole (Tyr and Trp) moieties do not take place efficiently, appropriate protection of these groups enables the substrates to undergo smooth photoinduced decarboxylative reactions.
- Maeda, Kousuke,Saito, Hikaru,Osaka, Kazuyuki,Nishikawa, Keisuke,Sugie, Mai,Morita, Toshio,Takahashi, Ichiro,Yoshimi, Yasuharu
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p. 1117 - 1123
(2015/01/30)
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- Processes for forming amide bonds and compositions related thereto
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The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.
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Page/Page column 21; 22
(2015/01/07)
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- Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds
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Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.
- Liu, Hui,Yang, Zhimin,Pan, Zhengying
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supporting information
p. 5902 - 5905
(2015/01/08)
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- Redox-triggered changes in the self-assembly of a ferrocene-peptide conjugate
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Ultrasonication of a ferrocene conjugate of a short amyloid peptide (Aβ18-20) in toluene causes formation of an organogel, which undergoes dramatic structural changes upon oxidation from a nanofibrillar network to spherical micelles. This morphological change is redox-controlled and reversible. the Partner Organisations 2014.
- Adhikari, Bimalendu,Kraatz, Heinz-Bernhard
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supporting information
p. 5551 - 5553
(2014/05/20)
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- Environmentally benign peptide synthesis using liquid-assisted ball-milling: Application to the synthesis of Leu-enkephalin
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This paper describes an original methodology for peptide bond synthesis avoiding toxic solvents and reactants. Ball-milling stoichiometric amounts of Boc-protected α-amino acid N-carboxyanhydrides (Boc-AA-NCA) or Boc-protected α-amino acid N-hydroxysuccin
- Bonnamour, Julien,Metro, Thomas-Xavier,Martinez, Jean,Lamaty, Frederic
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supporting information
p. 1116 - 1120
(2013/06/05)
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- Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors
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Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50=2.51±0.2 M) showed similar inhibitory effect compared with control compound Bestatin (IC50=6.25±0.4 M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.
- Pan, Huili,Yang, Kanghui,Zhang, Jian,Xu, Yingying,Jiang, Yuqi,Yuan, Yumei,Zhang, Xiaopan,Xu, Wenfang
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p. 717 - 726
(2013/07/26)
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- Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors
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A simple and straightforward method for the stereocontrolled synthesis of β-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high βselectivities (typically >70 % yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl). Copyright
- Zheng, Jianbin,Urkalan, Kaveri Balan,Herzon, Seth B.
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supporting information
p. 6068 - 6071
(2013/06/27)
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- Bispidine as a helix inducing scaffold: Examples of helically folded linear peptides
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We designed and synthesized bispidine-anchored peptides and showed that these peptides as small as B3 (containing four chiral α-amino acid residues) adopt a right handed helical conformation. Bispidine anchored linear peptide B3 adopts a helical conformat
- Haridas,Sadanandan, Sandhya,Gopalakrishna,Bijesh,Verma, Ram. P.,Chinthalapalli, Srinivas,Shandilya, Ashutosh
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supporting information
p. 10980 - 10982
(2013/11/19)
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- Antioxidant activity of peptide-based angiotensin converting enzyme inhibitors
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Angiotensin converting enzyme (ACE) inhibitors are important for the treatment of hypertension as they can decrease the formation of vasopressor hormone angiotensin II (Ang II) and elevate the levels of vasodilating hormone bradykinin. It is observed that bradykinin contains a Ser-Pro-Phe motif near the site of hydrolysis. The selenium analogues of captopril represent a novel class of ACE inhibitors as they also exhibit significant antioxidant activity. In this study, several di- and tripeptides containing selenocysteine and cysteine residues at the N-terminal were synthesized. Hydrolysis of angiotensin I (Ang I) to Ang II by ACE was studied in the presence of these peptides. It is observed that the introduction of l-Phe to Sec-Pro and Cys-Pro peptides significantly increases the ACE inhibitory activity. On the other hand, the introduction of l-Val or l-Ala decreases the inhibitory potency of the parent compounds. The presence of an l-Pro moiety in captopril analogues appears to be important for ACE inhibition as the replacement of l-Pro by l-piperidine 2-carboxylic acid decreases the ACE inhibition. The synthetic peptides were also tested for their ability to scavenge peroxynitrite (PN) and to exhibit glutathione peroxidase (GPx)-like activity. All the selenium-containing peptides exhibited good PN-scavenging and GPx activities. The Royal Society of Chemistry 2012.
- Bhuyan, Bhaskar J.,Mugesh, Govindasamy
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experimental part
p. 2237 - 2247
(2012/04/10)
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- In situ carboxyl activation using a silatropic switch: A new approach to amide and peptide constructions
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The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.
- Wu, Wenting,Zhang, Zhihui,Liebeskind, Lanny S.
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supporting information; experimental part
p. 14256 - 14259
(2011/11/05)
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- An amyloid-like fibril-forming supramolecular cross-β-structure of a model peptide: A crystallographic insight
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The peptide Boc-Val-Phe-OMe 1 bearing sequence similarity with the central hydrophobic cluster (CHC) of Alzheimer's Aβ18-19 peptide self-assembles to produce amyloid-like straight unbranched fibrils as examined by atomic force microscopy and Congo red assay. Single crystal X-ray diffraction offers the atomic level structure of the supramolecular parallel β-sheet aggregation and antiparallel separation between layers (cross-β-structure).
- Maity, Sibaprasad,Kumar, Pankaj,Haldar, Debasish
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experimental part
p. 3787 - 3791
(2011/06/27)
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- Solvent-free synthesis of peptides
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Chamical Equation Presentation A crush on sweetness! The coupling of a urethane-protected N-carboxyanhydride of an amino acid with another amino acid derivative under ball-milling conditions gives a protected dipeptide in very high yield (see scheme; PG: protecting group). The reaction takes place in the solid state. The synthesis was applied to the preparation of a tri peptide and the sweetener aspartame, without any organic solvent or purification.
- Declerck, Valerie,Nun, Pierrick,Martinez, Jean,Lamaty, Frederic
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supporting information; experimental part
p. 9318 - 9321
(2010/03/24)
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- The synthesis of functionalised peptides using α-lithio quinuclidine N-oxide (Li-QNO)
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Deprotonation of protected peptides using lithiated quinuclidine N-oxide (Li-QNO) as a base at 0 °C, followed by addition of an alkyl halide gives C-alkylated peptide derivatives in good yield.
- O'Neil, Ian A.,Bhamra, Inder
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supporting information; experimental part
p. 3635 - 3638
(2009/09/30)
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- Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors
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Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluate
- Shang, Luqing,Fang, Hao,Zhu, Huawei,Wang, Xuejian,Wang, Qiang,Mu, Jiajia,Wang, Binghe,Kishioka, Shiroh,Xu, Wenfang
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experimental part
p. 2775 - 2784
(2009/08/15)
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- Comprehensive study of sansalvamide A derivatives and their structure-activity relationships against drug-resistant colon cancer cell lines
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We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the
- Otrubova, Katerina,Lushington, Gerald,Vander Velde, David,McGuire, Kathleen L.,McAlpine, Shelli R.
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p. 530 - 544
(2008/09/18)
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- Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides
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(Formula Presented) Readily prepared amino thioacids react at room temperature in DMF in the presence of cesium carbonate with 2,4- dinitrobenzenesulfonamides to give amides. When the sulfonamide is derived from an amino acid the method results in peptide bond formation, whereas the use of carbohydrate derived sulfonamides gives neoglycoconjugates.
- Crich, David,Sana, Kasinath,Guo, Songpo
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p. 4423 - 4426
(2008/03/12)
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- Synthesis of second-generation Sansalvamide A derivatives: Novel templates as potential antitumor agents
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We report the synthesis of 34 second-generation Sansalvamide A derivatives. San A derivatives have unique anticancer properties and target multiple cancers, including colon, pancreatic, breast, prostate, and melanoma. As novel templates, the derivatives d
- Rodriguez, Rodrigo A.,Pan, Po-Shen,Pan, Chung-Mao,Ravula, Suchitra,Lapera, Stephanie,Singh, Erinprit K.,Styers, Thomas J.,Brown, Joseph D.,Cajica, Julia,Parry, Emily,Otrubova, Katerina,McAlpine, Shelli R.
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p. 1980 - 2002
(2007/10/03)
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- Structure-based design, synthesis, and biological evaluation of peptidomimetic SARS-CoV 3CLpro inhibitors
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Structure-based design, synthesis, and biological evaluation of a series of peptidomimetic severe acute respiratory syndrome-coronavirus chymotrypsin-like protease inhibitors are described. These inhibitors were designed and synthesized based upon our X-r
- Ghosh, Arun K.,Xi, Kai,Grum-Tokars, Valerie,Xu, Xiaoming,Ratia, Kiira,Fu, Wentao,Houser, Katherine V.,Baker, Susan C.,Johnson, Michael E.,Mesecar, Andrew D.
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p. 5876 - 5880
(2008/03/14)
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- Synthesis of Sansalvamide A derivatives and their cytotoxicity in the MSS colon cancer cell line HT-29
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We report the synthesis of thirty-six Sansalvamide A derivatives, and their biological activity against colon cancer HT-29 cell line, a microsatellite stable (MSS) colon cancer cell-line. The thirty-six compounds can be divided into three subsets, where t
- Styers, Thomas J.,Kekec, Ahmet,Rodriguez, Rodrigo,Brown, Joseph D.,Cajica, Julia,Pan, Po-Shen,Parry, Emily,Carroll, Chris L.,Medina, Irene,Corral, Ricardo,Lapera, Stephanie,Otrubova, Katerina,Pan, Chung-Mao,McGuire, Kathleen L.,McAlpine, Shelli R.
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p. 5625 - 5631
(2007/10/03)
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- Synthesis of a small library of diketopiperazines as potential inhibitors of calpain
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A small library of 2,5-diketopiperazines based on previously reported calpain inhibitors was synthesized. In addition, a concise total synthesis of the structurally related natural product phevalin (2) was accomplished. Despite literature reports that som
- Zeng, Yibin,Li, Qingshan,Hanzlik, Robert P.,Aube, Jeffrey
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p. 3034 - 3038
(2007/10/03)
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- β-sheet ligands in action: KLVFF recognition by aminopyrazole hybrid receptors in water
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Little is known about the precise mechanism of action of β-sheet ligands, hampered by the notorious solubility problems involved with protein misfolding and amyloid formation. Recently the nucleation site for the pathogenic aggregation of the Alzheimer's
- Rzepecki, Petra,Schrader, Thomas
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p. 3016 - 3025
(2007/10/03)
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- Synthesis and evaluation of tripeptidyl α-ketoamides as human rhinovirus 3C protease inhibitors
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We describe herein the synthesis and biological evaluation of a series of tripeptidyl α-ketoamides as human rhinovirus (HRV) 3C protease inhibitors. The most potent inhibitor discussed in this manuscript, 4I, exhibited impressive enzyme inhibitory activity as well as antiviral activity against HRV-14.
- Chen, Shu-Hui,Lamar, Jason,Victor, Frantz,Snyder, Nancy,Johnson, Robert,Heinz, Beverly A.,Wakulchik, Mark,Wang, Q. May
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p. 3531 - 3536
(2007/10/03)
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- Application of nim-2,6-dimethoxybenzoyl histidine in solid-phase peptide synthesis
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Fmoc-histidine derivatives protected with 2,6-dimethoxybenzoyl (2,6-Dmbz) units, either on the τ- (1) or on the π-position (2) of the imidazole residue, have been prepared and applied to the synthesis of the dipeptide Fmoc-His(2,6-Dmbz)-Val-OMe, with high coupling efficiencies (99 and 95%, respectively) and low racemization (0.3 and 0.1%, respectively), as ascertained by HPLC analysis on the fully protected dipeptides. In addition, the hexapeptide H-Ala-Ser-Val-His-Val-Phe-OH (I) has been synthesized on a solid support employing the novel building blocks 1 and 2 as well as commercially available Fmoc-His(t-Trt)-OH (3). The crude deprotected products were analyzed by reverse-phase HPLC and mass spectrometry, which indicated that when the τ-protected derivatives 1 and 3 were employed the products were of comparable quality (93-94% major peak). The hexapeptide synthesized with the π-protected histidine 2 was contaminated with a product corresponding to 2,6-Dmbz-His-Val-Phe-OH (12), which was probably formed through the intramolecular acyl transfer of a 2,6-Dmbz unit from the π-nitrogen atom to the α-amino group of the N-terminal histidine unit upon removal of the Fmoc group. This side reaction was insignificant (less than 0.5%) when using the τ-protected derivative 1. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
- Zaramella, Simone,Stroemberg, Roger,Yeheskiely, Esther
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p. 2454 - 2461
(2007/10/03)
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- Synthesis and properties of N-substituted saccharin derivatives
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Four different routes for the synthesis of saccharin containing peptids were studied. While reactions between saccharin sodium and α-halogeno acids were limited to two examples, reactions of sulfobenzoic anhydride (4) or saccharin-N-carboxylate (6) with amino acid esters yielded the ring opened products 5 and 7. Finally, we found, that the reaction between the benzoxathiol derivative 8 and amino acid derivatives represents a versatile route to the peptidic compounds 9 and 11. Hydrolysis and hydrogenolysis were studied, and by combination of the different routes the "saccharin tripeptides" 18 were obtained. Structures and stereochemistry were elucidated by spectroscopic and chromatographic methods. Selected compounds were tested as sweeteners of as inhibitors of elastase, but no exiting results were found.
- Soubh,Besch,Otto, Hans-Hartwig
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p. 384 - 392
(2007/10/03)
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- HIV protease inhibitors
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PCT No. PCT/AU95/00817 Sec. 371 Date Sep. 9, 1997 Sec. 102(e) Date Sep. 9, 1997 PCT Filed Dec. 4, 1995 PCT Pub. No. WO96/16950 PCT Pub. Date Jun. 6, 1996A HIV-1 protease inhibitor which includes a n-terminal cycle (A) or a C-terminal cycle (B) or both cyc
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- Expeditious amide-forming reactions using thiol esters
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The reaction of a 2-pyridylthiol ester with a dimethylaluminum amide leads to the rapid formation of the corresponding amide. The tolylthiol esters can be activated with silver trifluoroacetate and coupled even with poorly reactive amino compounds. (C) 20
- Kurosu, Michio
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p. 591 - 594
(2007/10/03)
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- A facile synthesis of amides from 9-fluorenylmethyl carbamates and acid derivatives
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A mild and convenient one-pot procedure for the synthesis of amides from 9-fluorenylmethyl carbamates and acids using potassium fluoride, triethylamine and various coupling reagents in DMF at room temperature is described. The scope of this procedure was also tested in the coupling of a variety of 9-fluorenylmethyloxycarbonyl-protected amines with active moieties such as anhydrides, acyl imidazolides, activated esters, tosyl chlorides, and acyl halides.
- Li, Wen-Ren,Chou, Hsueh-Hsuan
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- Solid-supported chloro[1,3,5]triazine. A versatile new synthetic auxiliary for the synthesis of amide libraries
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(equation presented) 2,4,6-Trichloro[1,3,5]triazine was loaded on different types of NH2-functionalized resins to give a new supported reagent. The best results, in term of yields products, were obtained using the chlorotriazine linked to a polystyrene-poly(ethylene glycol) resin. This reagent was employed for the solution-phase synthesis of different amides and dipeptides.
- Masala, Simonetta,Taddei, Maurizio
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p. 1355 - 1357
(2008/02/09)
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- Efficient synthesis of substituted oxopiperazines from amino acids
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The synthesis of substituted oxopiperazines, which may act as conformationally constrained peptide mimics, is reported. The synthesis is based on the cyclization of sulfonamide dipeptides with dibromoethane as the 1,2-dielectrophile. Alternatively, these
- Mohamed, Nazim,Bhatt, Ulhas,Just, George
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p. 8213 - 8216
(2007/10/03)
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- Regioselective structural and functional mimicry of peptides. Design of hydrolytically-stable cyclic peptidomimetic inhibitors of HIV-1 protease
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Hydrolytically-stable cyclic mimetics of the tripeptides Leu-Asn-Phe and Phe-Ile-Val were designed and incorporated into peptidic inhibitors, Ac-{Leu-Asn-Phe}-CHOHCH2-Pro-Ile-Val-NH2 and Ac-Leu-Val-Phe-CHOHCH2-{Phe-Ile-Val}-NH2, of HIV-1 protease. Structural mimicry has been established through molecular modeling and X-ray crystallographic studies of inhibitors bound to HIV-1 protease. Cyclic and acyclic inhibitors had similar conformations that were superimposable and formed similar interactions with the enzyme. Functional mimicry was demonstrated by comparable inhibition of the protease by acyclic and cyclic molecules. Further substitution of the residual acyclic Pro-Ile-Val or Leu-Val-Phe inhibitor components, with Pip-NHtBu or Boc-Phe, respectively, gave hydrolytically stable, water-soluble, lipophilic inhibitors of similar potency. The use of cycles to fix the conformations of amino acid sequences in peptides allows regioselective structural mimicry leading to functional mimicry and also permits localized structure-activity optimization in inhibitors of HIV-1 protease. This approach might be usefully applied to inhibitors of other proteins.
- Abbenante,March,Bergman,Hunt,Garnham,Dancer,Martin,Fairlie
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p. 10220 - 10226
(2007/10/03)
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- Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
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The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.
- Funasaki, Noriaki,Hada, Sakae,Neya, Saburo
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p. 1861 - 1867
(2007/10/02)
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- SOLID-PHASE SYNTHESIS OF PEPTIDES ON THE POLYMERIC SUPPORT TRILAR
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The solid-phase synthesis of peptides has been achieved using the polymeric support TRILAR proposed by the Biolar Scientific-Production Association (Olaine).
- Lubsandorzhieva, L. K.,Khalil', B.,Zheltukhina, G. A.,Evstigneeva, R. P.
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p. 226 - 230
(2007/10/02)
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- SYNTHESES OF CYCLOTETRAPEPTIDES, AM-TOXIN ANALOGS, CONTAINING α-HYDROXYALANINE
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Condensation of amide with α-keto acid to yield a α-hydroxyalanine (α-Hyala) or dehydroalanine residue was applied to syntheses of analogs of AM-toxins, cyclotetradepsipeptides.Cyclo(α-Hyala-L-Ala-L-Val-L-Phe-), cyclo(-α-Hyala-L-Ala-L-Hmb-L-Phe-) and cycl
- Shimohigashi, Yasuyuki,Izumiya, Nobuo
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p. 763 - 766
(2007/10/02)
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