Synthesis of retro-inverso peptides employing isocyanates of Nα-Fmoc-amino acids/peptide acids catalyzed by DMAP

被引:13
|
作者
Venkataramanarao, Rao [1 ]
Sureshbabu, Vommina V. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Bangalore 560001, Karnataka, India
关键词
EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; SYSTEM; AZIDES; AMIDES;
D O I
10.1016/j.tetlet.2006.10.066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Goldschmidt-Wick type reaction between isocyanates of N-alpha-Fmoc-amino acids/peptide acids and N-alpha-Boc-/Z-/ Bsmoc-amino acids catalyzed by DMAP leads to the incorporation of a reversed peptide bond. It was found to be a simple, efficient and clean reaction. All the retro-inverso peptides made were obtained as crystalline compounds in 70-92% yields. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9139 / 9141
页数:3
相关论文
共 50 条
  • [1] SYNTHESIS OF RETRO-INVERSO PEPTIDE NUCLEIC-ACIDS .2. OLIGOMERIZATION AND STABILITY
    KROTZ, AH
    BUCHARDT, O
    NIELSEN, PE
    TETRAHEDRON LETTERS, 1995, 36 (38) : 6941 - 6944
  • [2] SYNTHESIS OF RETRO-INVERSO PEPTIDE NUCLEIC-ACIDS .1. CHARACTERIZATION OF THE MONOMERS
    KROTZ, AH
    BUCHARDT, O
    NIELSEN, PE
    TETRAHEDRON LETTERS, 1995, 36 (38) : 6937 - 6940
  • [3] RETRO-INVERSO AMIDE BONDS BETWEEN TRIFUNCTIONAL AMINO-ACIDS
    DURR, H
    GOODMAN, M
    JUNG, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (06) : 785 - 787
  • [4] An efficient conversion of the carboxylic group of N-Fmoc α-amino acids/peptide acids into N-formamides employing isocyanates as key intermediates
    Sudarshan, N. S.
    Narendra, N.
    Hemantha, H. P.
    Sureshbabu, Vommina V.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25): : 9804 - 9807
  • [5] Curtius rearrangement using ultrasonication: Isolation of isocyanates of Fmoc-amino acids and their utility for the synthesis of dipeptidyl ureas
    Babu, VVS
    Kantharaju
    Tantry, SJ
    INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2005, 11 (02) : 131 - 137
  • [6] Curtius Rearrangement Using Ultrasonication: Isolation of Isocyanates of Fmoc-Amino Acids and Their Utility for the Synthesis of Dipeptidyl Ureas
    Vommina V. Suresh Babu
    Subramanyam J. Kantharaju
    International Journal of Peptide Research and Therapeutics, 2005, 11 : 131 - 137
  • [7] Fmoc/Trt amino acids: comparison to Fmoc/tBu amino acids in peptide synthesis
    Barlos, K
    Gatos, D
    Koutsogianni, S
    JOURNAL OF PEPTIDE RESEARCH, 1998, 51 (03): : 194 - 200
  • [8] Efficient synthesis of tetrazole analogues of amino acids and peptides employing Fmoc chemistry
    Shankar, N. A.
    Chennakrishna, G.
    Ramanarao, R. V.
    Sureshbabu, V. V.
    BIOPOLYMERS, 2007, 88 (04) : 534 - 534
  • [9] Synthesis of peptides employing Fmoc-amino acid chlorides and commercial zinc dust
    Gopi, HN
    Babu, VS
    TETRAHEDRON LETTERS, 1998, 39 (52) : 9769 - 9772
  • [10] Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents
    Babu, VVS
    Rao, RVR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (11): : 2328 - 2332