Synthesis of a beta-hexapeptide from (R)-2-aminomethyl-alkanoic acids and structural investigations

被引:133
作者
Hintermann, T [1 ]
Seebach, D [1 ]
机构
[1] ETH ZURICH,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND
关键词
alpha-branched beta-amino acids; diastereoselective synthesis; beta-peptides; CD-spectroscopy; 3(1) helix;
D O I
10.1055/s-1997-6117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The (R) alpha-branched beta-amino acid derivatives 3-5 with the side chains of alanine, valine and leucine are prepared by aminomethylation of acyloxazolidinones 2a-c and are used for the synthesis of the trifluoroacetate salt 9 of H(-beta(2)-HVal-beta(2)-HAla-beta(2)-HLeu)(2)-OH. The CD spectrum of compound 9 is compared with that of the isomer H(-beta(3)-HVal-beta(3)-HAla-beta(3)-HLeu)(2)-OH (1) built from the corresponding beta-branched beta-amino acids.
引用
收藏
页码:437 / &
页数:3
相关论文
共 8 条
  • [1] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES
    EVANS, DA
    URPI, F
    SOMERS, TC
    CLARK, JS
    BILODEAU, MT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8215 - 8216
  • [2] Enantioselective synthesis of beta-amino acids .7. Preparation of enantiopure alpha-substituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one.
    Juaristi, E
    Quintana, D
    Balderas, M
    GarciaPerez, E
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2233 - 2246
  • [3] MATTHEWS JL, 1997, ENANTIOSELECTIVE SYN, pCH2
  • [4] beta-peptides: Synthesis by Arndt-Eistert homologation with concomitant peptide coupling. Structure determination by NMR and CD spectroscopy and by X-ray crystallography. Helical secondary structure of a beta-hexapeptide in solution and its stability towards pepsin
    Seebach, D
    Overhand, M
    Kuhnle, FNM
    Martinoni, B
    Oberer, L
    Hommel, U
    Widmer, H
    [J]. HELVETICA CHIMICA ACTA, 1996, 79 (04) : 913 - 941
  • [5] Probing the helical secondary structure of short-chain beta-peptides
    Seebach, D
    Ciceri, PE
    Overhand, M
    Jaun, B
    Rigo, D
    Oberer, L
    Hommel, U
    Amstutz, R
    Widmer, H
    [J]. HELVETICA CHIMICA ACTA, 1996, 79 (08) : 2043 - 2066
  • [6] TALLEY JJ, 1990, Patent No. 0396526
  • [7] WUNSCH E, 1974, HOUBENWEYL SYNTHES 1, V15
  • [8] WUNSCH E, 1974, HOUBENWEYL SYNTHES 2, V15