Modified method of synthesis of N-substituted dithioesters of amino acids and peptides in the Pinner reaction

被引：0

作者：

Neugebauer, Witold ^{[1
,2
]}

Pinet, Eric ^{[1
]}

Kim, Munsok ^{[1
]}

Carey, Paul R. ^{[1
]}

机构：

[1] Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ont. K1A 0R6, Canada

[2] Département de Pharmacologie, Faculté de Médecine, Université de Sherbrooke, Sherbrooke, Que. J1H 5N4, Canada

来源：

Canadian Journal of Chemistry | 1996年 / 74卷 / 03期

关键词：

Addition reactions - Alcohols - Amino acids - Chemical activation - Derivatives - Hydrofluoric acid - Isotopes - Raman spectroscopy - Synthesis (chemical);

D O I：

暂无

中图分类号：

学科分类号：

摘要：

An improved method for the synthesis of dithioesters of amino acids and peptides has been developed. The syntheses have been carried out from the nitriles. The addition of thiol to the nitrile derivative in the Pinner step of dithioester synthesis was activated with hydrogen fluoride. A few examples of dithioester synthesis using liquid HF are described. Some novel dithioesters, which are model compounds for resonance Raman spectroscopic studies of dithioacylpapain intermediates, are described.

引用

页码：341 / 343

共 50 条

[41] SYNTHESIS OF N-SUBSTITUTED OF 6-AMINO HEXANE AND PARA-AMINO METHYL BENZOIC-ACIDS
GRABENKO, AD
DANCHENKO, MN
PELKIS, PS
UKRAINSKII KHIMICHESKII ZHURNAL, 1977, 43 (09): : 966 - 968
[42] A new method for the synthesis of N-substituted pyrroles
Hai Xue
Chinese Chemical Letters, 2010, 21 (11) : 1291 - 1294
[43] A new method for the synthesis of N-substituted pyrroles
Xue, Hai
Ma, Tao
Wang, Lin
Liu, Gang
CHINESE CHEMICAL LETTERS, 2010, 21 (11) : 1291 - 1294
[44] SYNTHESIS OF N-SUBSTITUTED ALPHA-AMINO-ACIDS BY ELECTROCARBOXYLATION OF IMINES WITH SACRIFICIAL METALLIC ANODES
SILVESTRI, G
GAMBINO, S
FILARDO, G
GAZZETTA CHIMICA ITALIANA, 1988, 118 (09): : 643 - 648
[45] Synthesis of glucosylamino heterocycles by desulfurization-condensation of glucosyl isothiocyanates with N-substituted amino acids
Gama, Y
Shibuya, I
Shimizu, M
SYNTHETIC COMMUNICATIONS, 1999, 29 (09) : 1493 - 1501
[46] AMINO-ACIDS AND PEPTIDES .21. N-SUBSTITUTED PYRROLIDONES AS INTERMEDIATES IN THE SYNTHESIS OF GAMMA-AMINOBUTYRIC AND ALPHA,GAMMA-DIAMINOBUTYRIC ACID PEPTIDES
PODUSKA, K
RUDINGER, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1957, 22 (04) : 1283 - 1292
[47] Synthesis and biological evaluation of N-substituted α-amino acids from 4-hydroxy coumarins
Chavda, M
Shah, A
Bhatt, S
Deo, K
Kundu, P
ARZNEIMITTELFORSCHUNG-DRUG RESEARCH, 2003, 53 (03): : 196 - 200
[48] Utilization of Fukuyama's sulfonamide protecting group for the synthesis of N-substituted α-amino acids and derivatives
Lin, XD
Dorr, H
Nuss, JM
TETRAHEDRON LETTERS, 2000, 41 (18) : 3309 - 3313
[49] The synthesis of hexahydrooxoepithiopyridinedicarboximides by the reaction of thioamides with N-substituted maleimides
Takido, T
Tamura, S
Sato, K
Kamijo, H
Nakazawa, T
Hata, T
Seno, M
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (02) : 437 - 443
[50] Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides
Chen, Liang
Sun, Jing
Xie, Ju
Yan, Chao-Guo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (27) : 6497 - 6507

← 1 2 3 4 5 →