THEONEGRAMIDE, AN ANTIFUNGAL GLYCOPEPTIDE FROM THE PHILIPPINE LITHISTID SPONGE THEONELLA-SWINHOEI

被引:91
作者
BEWLEY, CA [1 ]
FAULKNER, DJ [1 ]
机构
[1] UNIV CALIF SAN DIEGO,SCRIPPS INST OCEANOG,LA JOLLA,CA 92093
关键词
D O I
10.1021/jo00096a028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Theonegramide (2) is an antifungal glycopeptide consisting of arabinose joined to a bicyclic dodecapeptide that contains the unusual amino acids beta-hydroxyasparagine, isoserine, alpha-aminoadipic acid, 4'-bromo-3-methylphenylalanine,3-amino-4-hydroxy-6-methyl-8-phenylocta-5,7-dienoic acid, and the same histidinoalanine moiety previously observed in theonellamide F (1). The structure of theonegramide (2) was elucidated by analysis of spectral data and its absolute configuration was determined by GC-MS analysis using a chiral column packing.
引用
收藏
页码:4849 / 4852
页数:4
相关论文
共 11 条
  • [1] FAULKNER DJ, 1993, GAZZ CHIM ITAL, V123, P301
  • [2] BIOACTIVE MARINE METABOLITES .33. CYCLOTHEONAMIDES, POTENT THROMBIN INHIBITORS, FROM A MARINE SPONGE THEONELLA SP
    FUSETANI, N
    MATSUNAGA, S
    MATSUMOTO, H
    TAKEBAYASHI, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) : 7053 - 7054
  • [3] BIOACTIVE SPONGE PEPTIDES
    FUSETANI, N
    MATSUNAGA, S
    [J]. CHEMICAL REVIEWS, 1993, 93 (05) : 1793 - 1806
  • [4] REASSIGNMENT OF STEREOCHEMISTRY AND TOTAL SYNTHESIS OF THE THROMBIN INHIBITOR CYCLOTHEONAMIDE-B
    HAGIHARA, M
    SCHREIBER, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6570 - 6571
  • [5] MARINE NATURAL-PRODUCTS .23. 3 NEW CYTOTOXIC DIMERIC MACROLIDES, SWINHOLIDE-B AND SWINHOLIDE-C AND ISOSWINHOLIDE-A, CONGENERS OF SWINHOLIDE-A, FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI
    KOBAYASHI, M
    TANAKA, J
    KATORI, T
    KITAGAWA, I
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) : 2960 - 2966
  • [6] KOBAYASHI M, 1990, CHEM PHARM BULL, V38, P2409
  • [7] GAS-CHROMATOGRAPHIC SEPARATION OF CARBOHYDRATE ENANTIOMERS ON A NEW CHIRAL STATIONARY PHASE
    KONIG, WA
    BENECKE, I
    BRETTING, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (08): : 693 - 694
  • [8] BIOACTIVE MARINE METABOLITES .26. THEONELLAMIDE-F - A NOVEL ANTIFUNGAL BICYCLIC PEPTIDE FROM A MARINE SPONGE THEONELLA SP
    MATSUNAGA, S
    FUSETANI, N
    HASHIMOTO, K
    WALCHLI, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2582 - 2588
  • [9] 8 NEW CYTOTOXIC METABOLITES CLOSELY RELATED TO ONNAMIDE-A FROM 2 MARINE SPONGES OF THE GENUS THEONELLA
    MATSUNAGA, S
    FUSETANI, N
    NAKAO, Y
    [J]. TETRAHEDRON, 1992, 48 (39) : 8369 - 8376
  • [10] SYNTHESIS OF (S)-ISOSERINE
    MIYAZAWA, T
    AKITA, E
    ITO, T
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1976, 40 (08): : 1651 - 1652