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
收藏
页码:341 / 343
相关论文
共 50 条
  • [1] Modified method of synthesis of N-substituted dithioesters of amino acids and peptides in the Pinner reaction
    Neugebauer, W
    Pinet, E
    Kim, M
    Carey, PR
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (03): : 341 - 343
  • [2] Decarbonylative diarylation reaction of N-substituted α-amino acids
    Seong, MR
    Kim, TY
    Lee, HJ
    Kim, JN
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1999, 20 (05) : 609 - 610
  • [3] SYNTHESIS OF POLYMERIC N-HYDROXYSUCCINIMIDE ESTERS OF N-SUBSTITUTED AMINO-ACIDS AND PEPTIDES
    ROGOZHIN, SV
    DAVIDOVICH, YA
    SAMOILOVA, NA
    MIRONOVA, NV
    YURTANOV, AI
    ANDREEV, SM
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (02): : 356 - 360
  • [4] A NOVEL SYNTHESIS OF N-SUBSTITUTED AMINO-ACIDS
    NAIM, SS
    KHAN, NH
    SIDDIQUI, AA
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1980, 19 (07): : 622 - 624
  • [5] SYNTHESIS OF NEW N-SUBSTITUTED CINNAMOYL DERIVATIVES OF AMINO ACIDS
    Spasova, M. G.
    Ivanova, G. I.
    Pajpanova, T. I.
    Milkova, T. S.
    JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 262 - 262
  • [6] SYNTHESIS OF N-SUBSTITUTED AMINO SULFONIC ACIDS .3.
    ZEID, I
    MOUSSA, H
    ISMAIL, I
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1974, (11): : 1816 - 1819
  • [7] SYNTHESIS OF N-SUBSTITUTED AMINO SULFONIC ACIDS .2.
    ZEID, I
    ISMAIL, I
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1974, (04): : 667 - 670
  • [8] Choline esters of N-substituted amino acids. IX. Synthesis and cholinergic properties of β-dimethylaminoethyl esters of N-substituted amino acids
    Topuzyan V.O.
    Khachvakyan G.Y.
    Shakhbazyan L.V.
    Gerasimyan D.A.
    Pharmaceutical Chemistry Journal, 1997, 31 (1) : 23 - 26
  • [9] SYNTHESIS OF N-SUBSTITUTED AMINOSULFONIC ACIDS
    ZEID, I
    ISMAIL, I
    CHEMISTRY & INDUSTRY, 1973, (08) : 380 - 380
  • [10] SYNTHESIS OF N-SUBSTITUTED AMINOSULFONIC ACIDS
    ZEID, I
    ISMAIL, I
    HELFERIC.B
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 761 (JUL): : 118 - &