cas 2799-07-7, S-Trityl-L-cysteine | Articles data

Articles about 2799-07-7Total 24 be found

Article title
Article abstract
Author
Journal number and time
Download

Palladium Mediated Rapid Deprotection of N-Terminal Cysteine under Native Chemical Ligation Conditions for the Efficient Preparation of Synthetically Challenging Proteins
Facilitating the process of chemical protein synthesis is an important goal in order to enable the efficient preparation of large and novel protein analogues. Native chemical ligation, which is widely used in the synthesis and semisynthesis of proteins, has been going through several developments to expedite the synthetic process and to obtain the target protein in high yield. A key aspect of this approach is the utilization of protecting groups for the N-terminal Cys in the middle fragments, which bear simultaneously the two reactive groups, i.e., N-terminal Cys and C-terminal thioester. Despite important progress in this area, as has been demonstrated in the use of thiazolidine protecting group in the synthesis of over 100 proteins, finding optimal protecting group(s) remains a challenge. For example, the thiazolidine removal step is very slow (>8 h), and in some cases the applied conditions lead to undesired side reactions. Here we show that water-soluble palladium(II) complexes are excellent reagents for the effective unmasking of thiazolidine, enabling its complete removal within 15 min under native chemical ligation conditions. Moreover, palladium is also able to rapidly remove propargyloxycarbonyl-protecting group from the N-terminal Cys in a similar efficiency. The utility of the new removal conditions for both protecting groups is exemplified in the rapid and efficient synthesis of Lys34-ubiquitinated H2B and for the first time neddlyated peptides derived from cullin1. The current approach expands the use of palladium in protein chemistry and should significantly facilitate the chemical and semisynthesis of synthetically challenging proteins from multiple fragments.
Jbara, Muhammad,Maity, Suman Kumar,Seenaiah, Mallikanti,Brik, Ashraf
p. 5069 - 5075
(2016)
Read Online

3-Mercaptopropionic acid-mediated synthesis of peptide and protein thioesters
Peptides and proteins fragment sequence-specifically in the presence of 3-mercaptopropionic acid to afford thioesters which can be used in native chemical ligation reactions. The Royal Society of Chemistry.
Kang, Jaskiranjit,Richardson, Jonathan P.,MacMillan, Derek
p. 407 - 409
(2009)
Read Online

Elastase Inhibitor Cyclotheonellazole A: Total Synthesis and in Vivo Biological Evaluation for Acute Lung Injury
Acute lung injury/acute respiratory distress syndrome (ALI/ARDS) is one of the most common complications in COVID-19. Elastase has been recognized as an important target to prevent ALI/ARDS in the patient of COVID-19. Cyclotheonellazole A (CTL-A) is a nat
Chen, Yue,Cui, Yingjun,Deng, Yangping,Fu, Qiang,Jiang, Peng,Li, Jing,Lin, Jianping,Liu, Yang,Meng, Qing,Sun, Yuanjun,Wang, Liang,Wang, Mukuo,Xu, Honglei,Ye, Baijun,Zhang, Mengyi,Zhang, Songming,Zhang, Tingrong,Zhao, Xiuhe
(2022/01/27)

Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex
The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.
De La Fuente, M. Carmen,Jiménez, Carlos,Rodríguez, Jaime,Segade, Yuri,Valderrama, Katherine
supporting information
p. 340 - 345
(2021/01/13)

Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
(2021/01/18)

Polycysteine as a new type of radio-protector ameliorated tissue injury through inhibiting ferroptosis in mice
Amifostine has been the only small molecule radio-protector approved by FDA for decades; however, the serious adverse effects limit its clinical use. To address the toxicity issues and maintain the good potency, a series of modified small polycysteine peptides had been prepared. Among them, compound 5 exhibited the highest radio-protective efficacy, the same as amifostine, but much better safety profile. To confirm the correlation between the radiation-protective efficacy and the DNA binding capability, each of the enantiomers of the polycysteine peptides had been prepared. As a result, the l-configuration compounds had obviously higher efficacy than the corresponding d-configuration enantiomers; among them, compound 5 showed the highest DNA binding capability and radiation-protective efficacy. To our knowledge, this is the first study that has proved their correlations using direct comparison. Further exploration of the mechanism revealed that the ionizing radiation (IR) triggered ferroptosis inhibition by compound 5 could be one of the pathways for the protection effect, which was different from amifostine. In summary, the preliminary result showed that compound 5, a polycysteine as a new type of radio-protector, had been developed with good efficacy and safety profile. Further study of the compound for potential use is ongoing.
Zhang, Junling,Li, Kui,Zhang, Qianru,Zhu, Zhimei,Huang, Gongchao,Tian, Hongqi
(2021/02/26)

Design, Synthesis, and Conformation-Activity Study of Unnatural Bridged Bicyclic Depsipeptides as Highly Potent Hypoxia Inducible Factor-1 Inhibitors and Antitumor Agents
By carrying out structural modifications based on the bicyclic peptide structure of echinomycin, we successfully synthesized various powerful antitumor derivatives. The ring conformation in the obtained compounds was restricted by cross-linking with an unnatural bond. The prepared derivatives were demonstrated to strongly suppress the hypoxia inducible factor (HIF)-1 transcriptional activation and hypoxia induction of HIF-1 protein expression. Particularly, alkene-bridged derivative 12 exhibited remarkably potent cytotoxicity (IC50 = 0.22 nM on the MCF-7 cell line) and HIF-1 inhibition (IC50 = 0.09 nM), which considerably exceeded those of echinomycin. Conformational analyses and molecular modeling studies revealed that the biological activities were enhanced following restriction of the conformation by cross-linking through a metabolically stable and rigid bridge bond. In addition, we proposed a new globular conformation stabilized by intramolecular πstacking that can contribute to the biological effects of bicyclic depsipeptides. The developments presented in the current study serve as a useful guide to expand the chemical space of peptides in drug discovery.
Koike, Kota,Nagano, Masanobu,Ebihara, Masahiro,Hirayama, Tasuku,Tsuji, Mieko,Suga, Hiroaki,Nagasawa, Hideko
p. 4022 - 4046
(2020/06/08)

Tripeptide-induced modulation of mesenchymal stem cell biomechanics stimulates proliferation and wound healing
We demonstrate the ability of two tripeptides to promote proliferation and modulate the mechanical properties of human mesenchymal stem cells (hMSCs). Notably, Young's modulus of peptide-treated hMSCs was found to be ～2 fold higher compared to the control group. These peptides promoted wound healing in hMSCs, without stimulating osteogenic and adipogenic differentiation, thus showing high potential in vascular tissue engineering applications.
Ali, Rafat,Chattopadhyay, Naibedya,Kulkarni, Chirag,Kulkarni, Manish M.,Porwal, Konica,Sharma, Swati,Tewari, Deepshikha,Verma, Sandeep
supporting information
p. 3043 - 3046
(2020/03/18)

Aminothiol compound, preparation method of aminothiol compound and application of aminothiol compound in radiation protection
The invention discloses an aminothiol compound, a preparation method of the aminothiol compound and application of the aminothiol compound in radiation protection. The compound has a structure shown in the formula I in the description, wherein A1 is selected from -C(O)NR8-, -S(O)2-NR8-, -S(O)NR8- and -R7-NR8-, A2 is selected from carbonyl, sulfonyl, sulfinyl and substituted or unsubstituted C1-6 alkyl, R1, R2, R5 and R6 can be the same or not and are selected from hydrogen and substituted or unsubstituted C1-C5 alkyl or hetero alkyl, n is an integer from 0 to 20000, R3 and R4 are independently selected from hydrogen, X and substituted or unsubstituted C1-6 alkyl, X is selected from F, Cl, Br and I, R7 is selected from substituted or unsubstituted C1-C6 alkyl, and R8 is selected from hydrogen and substituted or unsubstituted C1-C6 alkyl. The compound has the effect of reducing biological injury caused by ionizing radiation and also has the effects of prolonging the lifetime of radiated animals and increasing the survival rate of the radiated animals.
-
Paragraph 0199; 0200; 0201; 0202

(2017/04/03)

A "catch-and-release" protocol for alkyne-tagged molecules based on a resin-bound cobalt complex for peptide enrichment in aqueous media
The development of new and mild protocols for the specific enrichment of biomolecules is of significant interest from the perspective of chemical biology. A cobalt-phosphine complex immobilised on a solid-phase resin has been found to selectively bind to a propargyl carbamate tag, that is, "catch", under dilute aqueous conditions (pH 7) at 4-°C. Upon acidic treatment of the resulting resin-bound alkyne-cobalt complex, the Nicholas reaction was induced to "release" the alkyne-tagged molecule from the resin as a free amine. Model studies revealed that selective enrichment of the alkyne-tagged molecule could be achieved with high efficiency at 4-°C. The proof-of-concept was applied to an alkyne-tagged amino acid and dipeptide. Studies using an alkyne-tagged dipeptide proved that this protocol is compatible with various amino acids bearing a range of functionalities in the side-chain. In addition, selective enrichment and detection of an amine derived from the "catch and release" of an alkyne-tagged dipeptide in the presence of various peptides has been accomplished under highly dilute conditions, as determined by mass spectrometry. Catch and release: The specific enrichment of alkyne-tagged molecules has been achieved by using cobalt beads. A cobalt complex bound to a resin was found to selectively "catch" a propargyl carbamate tag under dilute aqueous conditions (see scheme). Upon acidic treatment of the alkyne-cobalt complex, the Nicholas reaction was induced to "release" an amine. Studies using an alkyne-tagged dipeptide proved its compatibility with various amino acids and peptides under highly dilute conditions.
Miyazaki, Ayako,Asanuma, Miwako,Dodo, Kosuke,Egami, Hiromichi,Sodeoka, Mikiko
supporting information
p. 8116 - 8128
(2014/07/07)

A mild removal of Fmoc group using sodium azide
A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected Nα-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis. Graphical Abstract: [Figure not available: see fulltext.]
Chen, Chun-Chi,Rajagopal, Basker,Liu, Xuan Yu,Chen, Kuan Lin,Tyan, Yu-Chang,Lin, Fui,Lin, Po-Chiao
p. 367 - 374
(2014/03/21)

A tetrazine templated method for the synthesis of ternary conjugates
Conjugation is an important reaction that enables coupling of molecules. Many protocols exist for the synthesis of binary conjugates from two different molecules or for the polyvalent display of a single molecule. There aren't many methods for the synthesis of ternary conjugates. However, methods for ternary conjugation are important for understanding the interplay of interactions between three biomolecules (or any three molecules per se). A strategy for ternary bioconjugation using inverse electron demand Diels-Alder reaction with tetrazine is studied. Ternary conjugation was demonstrated by the reaction of a model glyco-peptide binary conjugate with a fluorescent tagged olefin. The Royal Society of Chemistry 2013.
Venkateswara Rao, Boddu,Dhokale, Snehal,Rajamohanan, Pattuparambil R.,Hotha, Srinivas
supporting information
p. 10808 - 10810
(2013/11/06)

Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities
Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test. As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group.
Silvia, Vertuani,Baldisserotto, Anna,Scalambra, Emanuela,Malisardi, Gemma,Durini, Elisa,Manfredini, Stefano
experimental part
p. 383 - 392
(2012/07/28)

Development of a new enzyme-responsive self-immolative spacer conjugate applicable to the controlled drug release
A new self-immolative spacer conjugate based on a chemical adaptor unit aiming at controlled releasing drugs was designed and synthesized. It releases a fluorophore which was used as a model drug via a spontaneous cyclization mechanism after cleavage of an enzyme substrate. This system was proved to be stable under physiological conditions and only decomposed triggered by enzyme. It provides a generic linkage allowing connection of a variety of drugs and targeted devices to the chemical adaptor.
Jin, Hui-Juan,Lu, Jing,Wu, Xue
experimental part
p. 3465 - 3469
(2012/08/08)

Cysteine prodrugs to treat schizophrenia and drug addiction
The present invention provides cysteine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
-
Page/Page column 19-20

(2010/12/29)

CYSTEINE AND CYSTINE PRODRUGS TO TREAT SCHIZOPHRENIA AND REDUCE DRUG CRAVINGS
The present invention provides cysteine and cystine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
-
Page/Page column 28

(2009/10/09)

GLUCOKINASE ACTIVATORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT
The present invention relates to new compounds of formula (1) exhibiting excellent activity for glucokinase, and pharmaceutical compositions comprising the same as an active ingredient.
-
Page/Page column 214

(2009/07/25)

S-NITROSOMERCAPTO COMPOUNDS AND RELATED DERIVATIVES
The present invention is directed to mercapto-based and S- nitrosomercapto-based SNO compounds and their derivatives, and their use in treating a lack of normal breathing control, including the treatment of apnea and hypoventilation associated with sleep, obesity, certain medicines and other medical conditions.
-
Page/Page column 93

(2010/01/07)

TRITYLATION REACTIONS BASED ON METALLIC CATALYSIS
The invention relates to a method for preparing tritylated compounds in which protic functional groups are protected with the triphenylmethyl group, method based on the homogeneous catalysis exercised by salts or metal complexes in organic solvents. The invention relates in particular to a method for the selective tritylation of some groups, obtained both directly and by selective detritylation, with methods based on metallic catalysis. The application to amino acids, typical substrates not suitable to be subjected as such to homogeneous tritylations in organic solvents, indicates the ability of the method to extend also to hydrophilic substrates. The method allows to obtain with high yield pertrityl amino acids, N-tritylamino acids or amino acids tritylated only in lateral chain, compounds which heretofore were either difficult to obtain in aqueous solvents or obtainable through indirect methods. All, in any case, are important intermediates in peptide synthesis.
-
Page/Page column 31-32

(2010/11/25)

ALPHA KETOAMIDE COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.
-
Page/Page column 63

(2008/06/13)

A magnetic biomimetic nanocatalyst for cleaving phosphoester and carboxylic ester bonds under mild conditions
As a result of the unique surface structure of nanospheres, Asp and His residues supported on a 12 nm maghemite nanoparticle worked collaboratively as a biomimetic nanocatalyst for hydrolyzing paraoxon (phosphoester) and 4-nitrophenyl acetate (carboxylic ester) in Milli-Q water (pH 7.0) at 37 °C, without employing extremes of pH or heavy metals. Our nanocatalyst could be facilely recovered via magnetic concentration. The isolated catalyst exhibited long-term stability, showing no significant loss of its catalytic activity for repeated uses after 3 months.
Zheng, Yan,Duanmu, Chuansong,Gao, Yong
p. 3215 - 3217
(2007/10/03)

Dynamic combinatorial libraries of disulfide cages in water
(Figure Presented) Dynamic combinatorial libraries (DCLs) containing water-soluble disulfide-linked cages (alongside macrocyclic structures) have been generated and characterized. Unlike most other strategies for generating molecular cages, the structures are held together by covalent bonds, which are formed under thermodynamic control. The diversity of the cages generated opens new possibilities for a generalized combinatorial strategy toward molecular encapsulation.
West, Kevin R.,Bake, Kyle D.,Otto, Sijbren
p. 2615 - 2618
(2007/10/03)

seco-Cyclothialidines: New concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties
seco-Cyclothialidines are a promising class of bacterial DNA gyrase B subunit inhibitors. A new seco-cyclothialidine derivative containing a dioxazine moiety, BAY 50-7952, was synthesized through a new concise pathway. One key step of the synthesis is the
Rudolph,Theis,Hanke,Endermann,Johannsen,Geschke
p. 619 - 626
(2007/10/03)