BIOSYNTHESIS OF FUNGAL METABOLITES .10. STRUCTURES AND BIOSYNTHESIS OF MULTICOLANIC, MULTICOLIC, AND MULTICOLOSIC ACIDS, NOVEL TETRONIC ACID METABOLITES OF PENICILLIUM MULTICOLOR

被引:21
作者
GUDGEON, JA [1 ]
HOLKER, JSE [1 ]
SIMPSON, TJ [1 ]
YOUNG, K [1 ]
机构
[1] UNIV LIVERPOOL,ROBERT ROBINSON LABS,LIVERPOOL L69 3BX,MERSEYSIDE,ENGLAND
关键词
D O I
10.1016/0045-2068(79)90058-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Multicolanic, multicolic, and multicolosic acids, metabolites of Penicillium multicolor, are shown by chemical transformations and spectroscopic methods to be 4-ylidenetetronic acids with structures (I), (II), and (III), respectively. The biosynthesis of these metabolites from acetate, via oxidative fission of preformed 6-pentylresorcylic acid is established by incorporation studies with [1-13C]-, [2-13C]-, [1,2-13C]acetate and ethyl [2-14C]-6-pentylresorcylate. © 1979.
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页码:311 / 322
页数:12
相关论文
共 17 条
  • [1] A NEW SYNTHESIS OF OLIVETOL
    ANKER, RM
    COOK, AH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1945, (MAY): : 311 - 313
  • [2] ENZYMIC FORMATION OF PENICILLIC ACID
    AXBERG, K
    GATENBECK, S
    [J]. FEBS LETTERS, 1975, 54 (01) : 18 - 20
  • [3] INTERMEDIATES IN PENICILLIC ACID BIOSYNTHESIS IN PENICILLIUM-CYCLOPIUM
    AXBERG, K
    GATENBECK, S
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (07): : 749 - 751
  • [4] TOTAL SYNTHESIS AND STEREOSTRUCTURE OF METHYL (E)-O-METHYLMULTICOLANATE, A 4-YLIDENETETRONIC ACID FROM PENICILLIUM-MULTICOLOR
    BEGLEY, MJ
    GEDGE, DR
    PATTENDEN, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (02) : 60 - 61
  • [5] BELCHER R, 1954, SEMIMICRO QUANTITATI, P160
  • [6] BIOSYNTHESIS OF FUNGAL XANTHONE RAVENELIN
    BIRCH, AJ
    BALDAS, J
    HLUBUCEK, JR
    SIMPSON, TJ
    WESTERMAN, PW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08): : 898 - 904
  • [7] STUDIES IN BIOCHEMISTRY OF MICRO-ORGANISMS .113. PENCOLIDE, A NITROGEN-CONTAINING METABOLITE OF PENCILLIUM MULTICOLOR GRIGORIEVAMANILOVA AND PORADIELOVA
    BIRKINSHAW, JH
    KALYANPUR, MG
    STICKINGS, CE
    [J]. BIOCHEMICAL JOURNAL, 1963, 86 (02) : 237 - &
  • [8] FELL SCM, 1979, J CHEM SOC CHEM COMM, V81
  • [9] USE OF SINGLY AND DOUBLY LABELED ACETATE-C-13 IN ELUCIDATION OF STRUCTURES AND BIOSYNTHESIS OF MULTICOLIC AND MULTICOLOSIC ACIDS, NEW TETRONIC ACIDS FROM PENICILLIUM-MULTICOLOR
    GUDGEON, JA
    HOLKER, JSE
    SIMPSON, TJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (16) : 636 - 638
  • [10] TETRONIC ACIDS
    HAYNES, LJ
    PLIMMER, JR
    [J]. QUARTERLY REVIEWS, 1960, 14 (03): : 292 - 315