- Selection of amino acids and the biomimetic synthesis of amido bond in the presence of β-CD
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A new method was developed to construct a special amido bond in the presence of β-cyclodextrin. This process is similar to peptide synthesis in organisms. NMR experiments were performed to investigate the possible mechanism. This work has potential application in biomimetic peptide synthesis.
- Su, Jie,Su, Fan,Ma, MingFang,Li, Shangyang,Xing, Pengyao,Hao, Aiyou
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Read Online
- Rapid regio- and enantioselectivities and kinetic resolution of dl-lysine by an effective supramolecular system in water
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Herein we reported an example of chiral recognition, regioselective and kinetic resolution of dl-lysine by supramolecular interactions in aqueous solution of β-cyclodextrin. High regio- (> 99%) and enantioselectivies (> 99%) are achieved in a short time ( 10 min) under mild conditions.
- Ma, Mingfang,Su, Jie,Sheng, Xiang,Su, Fan,Li, Shangyang,Xing, Pengyao,Hao, Aiyou
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Read Online
- Method for selective structural modification of L-lysine
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The invention belongs to the field of chemical synthesis, and particularly relates to a method for selective structural modification of L-lysine. According to a specific technical scheme in the invention, L-lysine is taken as a raw material, silicon dioxide nanoparticles surface-functionalized by beta-cyclodextrin are taken as a catalyst, water is taken as a solvent, and a reaction is performed for 3-5 hours at 25 DEG C in the presence of an amino protective agent to obtain a final product of the reaction; the final reaction product is subjected to standing, and an upper-layer product is takenand subjected to washing, separating and filtering to obtain selectively-modified L-lysine. The used catalyst is odorless and non-toxic; the synthesis method is simple; catalytic performance is excellent; product separation is easy; the catalyst can be repeatedly used; the method effectively solves the problem that a mixture of a common beta-cyclodextrin catalyzed product and cyclodextrin floatson a liquid level and is difficult to separate, simplifies post-treatment steps, reduces the use amount of an organic solvent, and greatly reduces the amount of waste liquid generated in the stage ofpurification.
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Paragraph 0025; 0043-0047
(2020/07/15)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 3583 - 3588
(2020/08/05)
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- Novel aminopeptidase n inhibitors with improved antitumor activities
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A series of aminopeptidase N (APN) inhibitors were designed and synthesized. Enzyme inhibitory, docking and antiproliferative studies were performed to evaluate the derived molecules. Molecule D15, with IC50 values of 10.9 μM, showed the best performance in the APN enzymatic inhibition assay. The binding pattern of molecule D9 and D15 in the active site of APN was predicted by docking studies. Hydrophobic and H-bond interactions were discovered to make key roles in the ligand-receptor bindings. Compared with the previous C7, several molecules such as D9, D14 and D15, exhibited significantly improved activities in inhibiting the growth of HL-60, ES-2, A549 and PLC cell lines.
- Wang, Qiang,Shi, Qiao,Huang, Lu
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- Novel aminopeptidase N inhibitors with improved antitumor activities
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A series of aminopeptidase N (APN) inhibitors were designed and synthesized. Enzyme inhibitory, docking and antiproliferative studies were performed to evaluate the derived molecules. Molecule D15, with IC50 values of 10.9 μM, showed the best performance in the APN enzymatic inhibition assay. The binding pattern of molecule D9 and D15 in the active site of APN was predicted by docking studies. Hydrophobic and H-bond interactions were discovered to make key roles in the ligand-receptor bindings. Compared with the previous C7, several molecules such as D9, D14 and D15, exhibited significantly improved activities in inhibiting the growth of HL-60, ES-2, A549 and PLC cell lines.
- Wang, Qiang,Shi, Qiao,Huang, Lu
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- Concise total synthesis of aplysinellamides A and B
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Concise and efficient total syntheses of bromotyrosine-derived metabolites aplysinellamides A and B, isolated from Australian marine sponge Aplysinella sp., have been accomplished in seven steps. A condensation between cinnamic acid and Boc-D-lysine methyl ester was applied to form the amide skeleton as a key step.
- Gan, Haifeng,Huang, Yu,Feng, Weiyang,Zhu, Wentong,Guo, Kai
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p. 336 - 339
(2015/08/11)
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- Using the 9-BBN group as a transient protective group for the functionalization of reactive chains of α-amino acids
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Achieving chemoselectivity is a longstanding challenge in chemical synthesis. This problem has been addressed using different approaches, but a definitive solution is still pending. For instance, in peptide chemistry, particularly with amino acids containing side chains functionalities with reactivity patterns similar to the main functional groups, such as aspartic and glutamic acids, and lysine and ornithine, specific semi-permanent protecting groups have been employed. The use of 9-borabicyclo[3.3.1]nonane (9-BBN-H) as a transient protective group for the selective protection of α-amino acids, which allows the chemoselective manipulation of the functional groups embedded in the side chains of the molecule, is described.
- Sanchez, Adrian,Calderon, Ernesto,Vazquez, Alfredo
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p. 1364 - 1372
(2013/07/05)
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- Decomposition of copper-amino acid complexes by oxalic acid dihydrate
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A facile approach to the synthesis of some side-chain-protected amino acids via oxalic acid dihydrate as the copper sequestering reagent is presented. The copper in the amino acid complex reacted with oxalic acid dihydrate to form insoluble cupric oxalate, with the free amino acid released. Compared with conventional methods, this method is convenient, inexpensive, and environmentally friendly.
- Liu, Yi,Jia, Genguang,Ling, Xin,Lan, Nuo,Zheng, Youguang,Li, Sai,Zhang, Ling,Liu, Ling,Zhang, Rongli,Xue, Yunsheng
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experimental part
p. 557 - 559
(2012/08/08)
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- Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group
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In order to deprotect N-carbobenzoxy-l-aminoacids (Cbz-AA) and related compounds, a series of microorganisms was selected from soil by enrichment cultures with Cbz-l-Glu as sole nitrogen source. A lyophilized whole-cell preparation of two Arthrobacter sp. strains grown on Cbz-Glu or Cbz-Gly exhibited a high cleavage activity. The conditions of hydrolysis have been optimized and a quantitative enantioselective deprotection of several Cbz-dl-amino acids was obtained, as well as the deprotection of N-carbamoylester derivatives of several synthetic amino compounds. The preparation of Cbz-d-allylglycine and l-allylglycine in high yield and high optical purity is described as an application of this method.
- Maurs, Michele,Acher, Francine,Azerad, Robert
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- Engineered Thermoplasma acidophilum factor F3 mimics human aminopeptidase N (APN) as a target for anticancer drug development
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Human aminopeptidase N (hAPN) is an appealing objective for the development of anti-cancer agents. The absence of mammalian APN experimental structure negatively impinges upon the progression of structure-based drug design. Tricorn interacting factor F3 (factor F3) from Thermoplasma acidophilum shares 33% sequence identity with hAPN. Engineered factor F3 with two point directed mutations resulted in a protein with an active site identical to hAPN. In the present work, the engineered factor F3 has been co-crystallized with compound D24, a potent APN inhibitor introduced by our lab. Such a holo-form experimental structure helpfully insinuates a more bulky pocket than Bestatin-bound Escherichia coli APN. This evidence discloses that compound D24 targetting the structure of E. coli APN cannot bind to the activity cleft of factor F3 with high affinity. Thus, there is a potential risk of inefficiency to design hAPN targeting drug while using E. coli APN as the target model. We do propose here now that engineered factor F3 can be employed as a reasonable alternative of hAPN for drug design and development.
- Su, Jing,Wang, Qiang,Feng, Jinhong,Zhang, Cong,Zhu, Deyu,Wei, Tiandi,Xu, Wenfang,Gu, Lichuan
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scheme or table
p. 2991 - 2996
(2011/06/21)
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- Design, synthesis and preliminary activity evaluation of novel L-lysine derivatives as aminopeptidase N/CD13 inhibitors
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A novel class of L-lysine derivatives as aminopeptidase N (APN) inhibitors was designed and synthesized. Activity evaluation showed that compound C7 (IC50 = 9.6 ± 1.3 μM) and C20 (IC50 = 13.6 ± 1.9 μM) were equivalent to the positive control Bestatin (IC50 = 11.3 ± 1.6 μM).
- Wang, Qiang,Xu, Fuming,Mou, Jiajia,Zhang, Jian,Shang, Luqing,Luan, Yepeng,Yuan, Yumei,Liu, Yingzi,Li, Minyong,Fang, Hao,Wang, Binghe,Xu, Wenfang
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scheme or table
p. 847 - 853
(2011/12/04)
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- Design, synthesis, and QSAR studies of novel lysine derives as amino-peptidase N/CD13 inhibitors
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A series of novel l-lysine derivatives were designed, synthesized, and assayed for their inhibitory activities on amino-peptidase N (APN)/CD13 and matrix metalloproteinase-2 (MMP-2). The preliminary biological test showed that most of the compounds displayed a high inhibitory activity against MMP-2 and a low activity against APN except compound B6 which exhibited good potency (IC50 = 13.2 μM) similar with APN inhibitor Bestatin (IC50=15.5 μM), and could be used as lead compound in the future.
- Wang, Qiang,Chen, Maoying,Zhu, Huawei,Zhang, Jie,Fang, Hao,Wang, Binghe,Xu, Wenfang
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p. 5473 - 5481
(2008/12/21)
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- PROCESS FOR THE PREPARATION OF ε-ALKOXYCARBONYLLYSINES AND THEIR ANALOGUES
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A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1- alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε- alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.
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Page/Page column 17
(2008/06/13)
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- Decomposition of copper-amino acid complexes by sodium sulfide
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Sodium sulfide very efficiently removes copper from protected amino acid-copper complexes. The copper in the amino acid complex was reduced to insoluble cuprous sulfide and the free amino acid was released in pure form. This method is very convenient and rapid, requiring only 5-10 min and 0.55-0.75 equiv of sodium sulfide.
- Nowshuddin, Shaik,Reddy, A. Ram
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p. 5159 - 5161
(2007/10/03)
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- ACE-INHIBITORS HAVING ANTIOXIDANT AND NO-DONOR ACTIVITY
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Multifonctional ACE inhibitor compounds are provided, that combine ACE-inhibiting activity with capability to scavenge superoxide and other reactive oxygen species, and that may further function as nitric oxide donors. The compounds are useful for preventing or treating various disorders, including cardiovascular, and diabetes associated disorders.
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Page/Page column 61; 62
(2010/02/07)
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- Tetrachloroethylene oxide: hydrolytic products and reactions with phosphate and lysine.
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Tetrachloroethylene, or perchloroethylene (PCE), has considerable industrial use and is of toxicological interest because of a variety of effects. Most of the existing literature presents PCE oxide as a critical intermediate in the oxidative metabolism of PCE to Cl(3)CCO(2)H, oxalic acid, and products covalently bound to proteins, including trichloroacetyl derivatives of lysine. PCE oxide was synthesized by photochemical oxidation of PCE and characterized. Decomposition at neutral pH (t(1/2) = 7.9 min at 0 degrees C, 5.8 min at 23 degrees C, 2.6 min at 37 degrees C) yielded only trace ( approximately 1%) Cl(3)CCO(2)H; the major products identified were CO (73% yield) and CO(2) (63% yield). In phosphate buffer (0.10 M) a major product was identified as oxalyl phosphate. Oxalyl chloride also reacted to form CO and CO(2) in aqueous solution and to form oxalyl phosphate in neutral phosphate buffer. Oxalyl phosphate decomposed to oxalic acid (t(1/2) = 53 min at 37 degrees C) but did not react with lysine. Reaction of PCE oxide with free lysine yielded the oxalic acid amide derivatives of lysine plus lysine dimers in which cross-linking of the amino groups involved oxalo linkage. The reaction of PCE oxide with albumin yielded mainly N(6)-oxalolysine and some (5%) N(6)-trichloroacetyllysine. We propose a reaction pathway for PCE oxide based on our previous studies with trichloroethylene oxide, in which C-C bond scission is a major product of reaction in aqueous buffer and yields CO and CO(2). Oxalyl species are proposed as intermediates and prominent acylating species formed in the reactions of the epoxide. The formation of Cl(3)CCO(2)H in cytochrome P450 reactions is postulated to result from intramolecular migration within an enzyme intermediate.
- Yoshioka, Tadao,Krauser, Joel A,Guengerich, F Peter
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p. 1096 - 1105
(2007/10/03)
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- Process for the production of alkoxycarbonyl-dipeptides intermediates in the synthesis of the lisinopril
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Process for the production of alkoxycarbonyldipeptides intermediates in the synthesis of the lisinopril which comprises protecting both amino functions of the L-lysine with an alkoxycarbonyl group, subsequently making the N-carboxyanhydride of the N6-[alkoxycarbonyl]-L-lysine by treatment with thionyl chloride and making the desired alkoxycarbonyldipeptide by reaction with L-proline in alkaline medium.
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- Process for the production of alkoxycarbonylpeptides intermediates in the synthesis of the lisinopril
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Process for the production of alkoxycarbonyldipeptides intermediates in the synthesis of the lisinopril which comprises protecting both amino functions of the L-lysine with an alkoxycarbonyl group, subsequently making the N-carboxyanhydride of the N6-[alkoxycarbonyl]-L-lysine by treatment with thionyl chloride and making the desired alkoxycarbonyldipeptide by reaction with L-proline in alkaline medium.
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- A general diastereoselective synthesis of spiroacetals related to those in ionophores via the reaction of lactones with cerium(III) γ-cerioalkoxide. MAD reverses the diastereoselectivity of the addition of methylmetallics to a β-keto ether
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The following steps constitute a fairly general and stereoselective synthesis of spiroacetals. 1. Thiophenol is added to acrylic acid. 2. The latter is treated consecutively with butyllithium, CeCl3, and an organolithium compound. 3. The resulting 3-(phenylthio) ketone is either reduced in the presence of zinc ion to yield mainly one diastereomer or treated with methyllithium or methylmagnesium chloride in the presence or absence of methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD, 25) to yield selectively either of two diastereomeric 3-(phenylthio) alcohols. 4. The alcohol is treated with butyllithium, lithium 4,4'-di-tert-butylbiphenylide (LDBB), and CeCl3, to yield a cerium(III) γ-cerioalkoxide, which is added to a lactone, the reaction being quenched with acid. In the addition to the keto ether in the absence of MAD, methyllithium or methylmagnesium chloride give very predominantly the erythro alcohol, presumably via Cram's chelate model, while in the presence of excess MAD, the threo product is very predominant, possibly because each oxygen atom is complexed with the bulky aluminum reagent. The methodology is demonstrated by the preparation of diastereomeric spiroacetals related to those found in a number of natural ionophores by using as the reaction partner of the carboxylate salt, α-lithio tetrahydrofuran or tetrahydropyran, readily generated by reductive lithiation of the corresponding α-(phenylthio) heterocycle with LDBB, and by employing methylmetallics rather than reducing agents for the reaction with the ketone.
- Ahn,Cohen
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p. 3142 - 3150
(2007/10/02)
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- Acceleration of the N(α)-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1
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In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile α-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N(α)-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and N(G)-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.
- Tamamura,Nakamura,Noguchi,Funakoshi,Fujii
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p. 954 - 957
(2007/10/02)
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- Synthesis of Unnatural Amino Acids
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This communication presents efficient synthetic procedures for the D and L isomers of Nα-tert-butyloxycarbonyl-Nε-benzyloxycarbonyl-Nε-isopropyllysine dicyclohexylamine salt (Nα-Boc-Nε-Z-Ilys DCHA salt), the D and L isomers of Nα-tert-butyloxycarbonyl-Nεnicotinoyllysine (Nα-Boc-Niclys), β-(3-quinolyl)-D,L-alanine (3-Quinal), and the resolution into the D and L isomers of 3-Quinal.
- Acosta, C. Kirk,Bahr, Martin L.,Burdett, James E.,Cessac, James W.,Martinez, Rudy A.,et al.
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p. 914 - 934
(2007/10/02)
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- New Reagents to Decompose Copper Complexes of Amino Acids
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The use of N,N-dialkyl-N'-(benzoyl)thioureas in ethanol is an effective method to decompose copper complexes of amino acids.The reaction gives optimal yields, and no racemisation is observed.Furthermore, the recovery of the thiourea derivatives is an important advantage of this method.
- Koenig, Karl-Heinz,Kaul, Lothar,Kuge, Martin,Schuster, Michael
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p. 1115 - 1116
(2007/10/02)
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- INVESTIGATION ON PEPTIDE SYNTHESIS BY FRAGMENT CONDENSATION. PART I. SYNTHESIS OF C1 - C4 FRAGMENT OF SUBSTANCE P IN SOLUTION AND BY THE SOLID PHASE METHOD
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The synthesis of protected tetrapeptide Z3-Arg-Pro-Lys(Z)-Pro-OH corresponding to C1 - C4 fragment of substance P in solution and by the solid phase method has been elaborated.
- Orlowska, Alicja,Drabarek, Stefania
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p. 1893 - 1899
(2007/10/02)
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