Conjugate addition of amino acid side chains to alkynones and alkynoic acid derivatives

被引:33
|
作者
Crisp, GT [1 ]
Millan, MJ [1 ]
机构
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
关键词
D O I
10.1016/S0040-4020(97)10323-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Suitably protected amino acids were used to investigate the Michael addition of the sulfanyl group of cysteine, the hydroxyl group of serine and the epsilon-amino group of lysine to a conjugated alkynone, alkynoic ester and alkynoic amide. The expected heterosubstituted vinyl product was formed in each case. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:637 / 648
页数:12
相关论文
共 50 条
  • [41] Strengths of hydrogen bonds involving phosphorylated amino acid side chains
    Mandell, Daniel J.
    Chorny, Ilya
    Groban, Eli S.
    Wong, Sergio E.
    Levine, Elisheva
    Rapp, Chaya S.
    Jacobson, Matthew P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) : 820 - 827
  • [42] Solvation thermodynamics of amino acid side chains on a short peptide backbone
    Hajari, Timir
    van der Vegt, Nico F. A.
    JOURNAL OF CHEMICAL PHYSICS, 2015, 142 (14):
  • [43] Functional Properties of Amino Acid Side Chains as Biomarkers of Extraterrestrial Life
    Georgiou, Christos D.
    ASTROBIOLOGY, 2018, 18 (11) : 1479 - 1496
  • [44] NATURE OF AMINO ACID SIDE CHAINS WHICH ARE CRITICAL FOR ACTIVITY OF LYSOZYME
    PARSONS, SM
    JAO, L
    DAHLQUIS.FW
    BORDERS, CL
    GROFF, T
    RACS, J
    RAFTERY, MA
    BIOCHEMISTRY, 1969, 8 (02) : 700 - &
  • [45] DNA-catalyzed covalent modification of amino acid side chains
    Wong, On Yi
    Pradeepkumar, P. I.
    Silverman, Scott K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [46] Mercedes Benz model of neutral amino-acid side chains
    Becker, Jean-Paul
    Collet, Olivier
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2006, 774 (1-3): : 23 - 28
  • [47] Proton Affinities of Some Amino Acid Side Chains in a Restricted Environment
    Abi, T. G.
    Anand, Amit
    Taraphder, Srabani
    JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (28): : 9570 - 9576
  • [48] Entropy and enthalpy of interaction between amino acid side chains in nanopores
    Vaitheeswaran, S.
    Thirumalai, D.
    JOURNAL OF CHEMICAL PHYSICS, 2014, 141 (22):
  • [49] PHILICITY OF AMINO-ACID SIDE-CHAINS FOR PHOTOGENERATED CARBENES
    SIGRIST, H
    MUHLEMANN, M
    DOLDER, M
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1990, 7 (2-4) : 277 - 287
  • [50] CONFORMATIONAL PREFERENCES OF AMINO-ACID SIDE-CHAINS IN COLLAGEN
    NEMETHY, G
    SCHERAGA, HA
    BIOPOLYMERS, 1982, 21 (08) : 1535 - 1555