Synthesis and spectroscopic characterization of β-di-, β-tri-, and β-hexapeptides built with (S)-2-methylene-3-aminoalkanoic acids derived from alanine, valine, and leucine

被引:9
作者
Bierbaum, DJ [1 ]
Seebach, D [1 ]
机构
[1] ETH Honggerberg, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland
关键词
D O I
10.1071/CH04052
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Methylthiomethylation and subsequent sulfoxidation and pyrolysis of the N-Boc-protected beta(3)-amino acid methyl esters derived from Ala, Val, and Leu provided the alpha-methylene esters; these were then used to synthesize the beta-peptides specified in the title (step-by-step and fragment coupling in solution). The novel beta-peptides were fully characterized, but neither solid-state nor solution structures were found.
引用
收藏
页码:859 / 863
页数:5
相关论文
共 38 条
  • [1] Abele S, 1999, HELV CHIM ACTA, V82, P1559, DOI 10.1002/(SICI)1522-2675(19991006)82:10<1559::AID-HLCA1559>3.3.CO
  • [2] 2-1
  • [3] Abele S, 2000, EUR J ORG CHEM, V2000, P1
  • [4] Synthesis and structural characterization of helix-forming β-peptides:: trans-2-aminocyclopentanecarboxylic acid oligomers
    Appella, DH
    Christianson, LA
    Klein, DA
    Richards, MR
    Powell, DR
    Gellman, SH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7574 - 7581
  • [5] Bodanszky M., 1994, The Practice of Peptide Synthesis, V2nd
  • [6] Flat peptides
    Crisma, M
    Formaggio, F
    Toniolo, C
    Yoshikawa, T
    Wakamiya, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) : 3272 - 3278
  • [7] Eliel E.L., 1994, Stereochemistry of Organic Compounds
  • [8] DIASTEREOSELECTIVE ALKYLATION OF 3-AMINOBUTANOIC ACID IN THE 2-POSITION
    ESTERMANN, H
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1988, 71 (07) : 1824 - 1839
  • [9] Can one derive the conformational preference of a β-peptide from its CD spectrum?
    Glättli, A
    Daura, X
    Seebach, D
    van Gunsteren, WF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 12972 - 12978
  • [10] Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
    Humphrey, JM
    Chamberlin, AR
    [J]. CHEMICAL REVIEWS, 1997, 97 (06) : 2243 - 2266