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
  • [31] First synthesis of N-substituted amino and N-sulfonylaminated methylthiopyrimidines:: Reaction of dimethyl N-cyanodithioiminocarbonate with substituted hydrazides
    Elgemeie, GH
    Sood, SA
    SYNTHETIC COMMUNICATIONS, 2006, 36 (06) : 743 - 753
  • [32] Synthesis of N-substituted 3-aminomethylidenetetramic acids
    Pirc, S
    Bevk, D
    Jakse, R
    Recnik, S
    Golic, L
    Golobic, A
    Meden, A
    Stanovnik, B
    Svete, J
    SYNTHESIS-STUTTGART, 2005, (17): : 2969 - 2988
  • [33] SYNTHESIS OF N-SUBSTITUTED AMIDES OF UNSATURATED-ACIDS
    FARAFONTOVA, VI
    PODGORNOVA, VA
    USTAVSHCHIKOV, BF
    JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1976, 49 (04): : 979 - 981
  • [34] SYNTHESIS OF N-SUBSTITUTED 2-AMINOETHANETHIOSULFURIC ACIDS
    KLAYMAN, DL
    GILMORE, WF
    JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (06) : 823 - &
  • [35] SYNTHESIS OF N-SUBSTITUTED MALEAMIC ACIDS AS POTENTIAL HYPOCHOLESTEREMICS
    LIU, KC
    CHEN, TB
    JAN, HJ
    SHIH, CY
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1973, 20 (03) : 163 - 169
  • [36] SYNTHESIS OF N-SUBSTITUTED ALPHA-AMINOARYLMETHANEPROPADIENEPHOSPHONIC ACIDS
    BELAKHOV, VV
    YUDELEVICH, VI
    KOMAROV, EV
    IONIN, BI
    PETROV, AA
    ZHURNAL OBSHCHEI KHIMII, 1984, 54 (01): : 226 - 228
  • [37] Sialic acid aldolase-catalyzed condensation of pyruvate and N-substituted mannosamine: A useful method for the synthesis of N-substituted sialic acids
    Lin, CC
    Lin, CH
    Wong, CH
    TETRAHEDRON LETTERS, 1997, 38 (15) : 2649 - 2652
  • [38] N-Substituted amino acids as anticorrosion additives. Part III: N-Acyl amino acids
    Telegdi, J.
    INTERNATIONAL JOURNAL OF CORROSION AND SCALE INHIBITION, 2016, 5 (03): : 263 - 272
  • [39] THE REACTION OF ENONES WITH N-SUBSTITUTED HYDRAZINES AND N-SUBSTITUTED UREAS
    KASHIMA, C
    YOSHIWARA, N
    HETEROCYCLES, 1985, 23 (01) : 171 - 171
  • [40] REACTION OF N-SUBSTITUTED AMINO-ORTHO-QUINONES WITH ETHYLENEDIAMINE
    CHERNYAK, SA
    TSIZIN, YS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (07): : 959 - 962