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 Найдено в других БД:Публикации Чарушина В.Н. (1)
Формат представления найденных документов:
полныйинформационныйкраткий
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авторузаглавиюгоду изданиятипу документа
Поисковый запрос: (<.>K=DIPEPTIDES<.>)
Общее количество найденных документов : 4
Показаны документы с 1 по 4
1.
Инвентарный номер: нет.
   
   S 90


   
    Study of the effect of the nature of the side chain in esters of amino acids on the diastereoselectivity of condensation with 5(4H)-oxazolone in the synthesis of dipeptides with N-terminal N-acetylphenylalanine [Electronic resource] / V. P. Krasnov, E. A. Zhdanova, N. Z. Solieva, L. Sh. Sadretdinova, I. M. Bukrina, A. M. Demin, G. L. Levit, M. A. Ezhikova, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1331-1334
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Conditions for fast racemization of 5(4H)-oxazolones prepared from N-acylphenylalanine were found. Reactions of 4-benzyl-2-methyl-5(4H)-oxazolone with amino acid esters proceed diastereoselectively to give predominantly dipeptides comprising R-phenylalanine. The diastereoselectivity increases with complication of the structure of the side chain in the amino acid esters

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1331.pdf
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2.
Инвентарный номер: нет.
   
   S 90


   
    Study of the inf luence of the alkyl ester group in (S)-valinates on diastereoselectivity of their condensation with N-acetylphenylalanine by the mixed anhydride method [Electronic resource] / E. A. Zhdanova, N. Z. Solieva, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 5. - P925-927. - Bibliogr. : p. 927 (15 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
5(4H)-OXAZOLONES -- AMINO ACIDS -- DIASTEREOSELECTIVITY -- DIPEPTIDES -- DYNAMIC KINETIC RESOLUTION -- RACEMIZATION
Аннотация: The dynamic kinetic resolution in the synthesis of alkyl N-acetylphenylalanyl (S)-valinates was studied by the mixed anhydride method. The structure of the ester group of the amino component appeared to exert no substantial effect on the diastereoselectivity of the reaction.

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (5), 925.pdf
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3.
Инвентарный номер: нет.
   
   S 98


   
    Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides [Electronic resource] / V. P. Krasnov, A. Yu. Vigorov, V. V. Musiyak, I. A. Nizova, D. A. Gruzdev, T. V. Matveeva, G. L. Levit, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2016. - Vol. 26, № 11. - С. 2645-2648
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PURINE -- GLUTAMIC ACID -- AMINO ACIDS
Аннотация: Synthetic routes to novel N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates with amino acids and glycine-containing dipeptides were developed. In vitro testing of 42 new and known compounds made it possible to reveal a series of N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates exhibiting significant antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant M. tuberculosis strain isolated from tuberculosis patients in the Ural region (Russia). N-(2-Aminopurin-6-yl)- and N-(purin-6-yl)-glycyl-(S)-glutamic acids were the most active compounds. (C) 2016 Elsevier Ltd. All rights reserved

\\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2016, v. 26, p. 2645.pdf
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4.
Инвентарный номер: нет.
   
   S 83


   
    Stereochemical aspects in the synthesis of novel N-(purin-6-yl)dipeptides as potential antimycobacterial agents / V. V. Musiyak, I. A. Nizova, E. N. Chulakov [et al.] // Amino Acids. - 2021. - Vol. 53, № 3. - P407-415
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DIPEPTIDES -- RACEMIZATION -- PURINE -- COUPLING -- NUCLEOPHILIC SUBSTITUTION -- ANTIMYCOBACTERIAL ACTIVITY
Аннотация: The synthesis of purine conjugates with natural amino acids is one of the promising directions in search for novel therapeutic agents, including antimycobacterial agents. The purpose of this study was to synthesize N-(purin-6-yl)dipeptides containing the terminal fragment of (S)-glutamic acid. To obtain the target compounds, two synthetic routes were tested. The first of them is based on coupling of N-(purin-6-yl)-(S)-amino acids to dimethyl (S)-glutamate in the presence of carbodiimide coupling agent followed by the removal of ester groups. However, it turned out that this coupling process was accompanied by racemization of the chiral center of N-(purin-6-yl)-α-amino acids and in all cases led to mixtures of (S,S)- and (R,S)diastereomers (6:4). Individual (S,S)-diastereomers were obtained using an alternative approach based on the nucleophilic substitution of chlorine in 6-chloropurine or 2-amino-6-chloropurine with corresponding dipeptides as nucleophiles. The enantiomeric purity of the target compounds was confirmed by chiral HPLC. To test the assumption that racemization of the chiral center of N-(purin-6-yl)-α-amino acids occurs with the participation of nitrogen atoms of the imidazole ring via the stage of formation of a chirally labile intermediate, we obtained such structural analogs of N-(purin-6-yl)-(S)-alanine as N-(9-benzylpurin-6-yl)-(S)-alanine and N-(7-deazapurin-6-yl)-(S)-alanine. It was found that coupling of these compounds to dimethyl (S)-glutamate was also accompanied by racemization. This indicates that the imidazole fragment does not play a crucial role in this process. When testing the antimycobacterial activity of some of the obtained compounds, conjugates with moderate activity against the laboratory Mycobacterium tuberculosis H37Rv strain (MIC 3.1–6.25 μg/mL) were identified.

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