The biosynthetic origin of diketopiperazines derived from D-proline

被引:31
作者
Bull, SD [1 ]
Davies, SG [1 ]
Parkin, RM [1 ]
Sánchez-Sancho, F [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期
关键词
D O I
10.1039/a802702a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Investigations reveal that the structures assigned to D-a-amino acid containing diketopiperazines (DKPs) 21-25 isolated from the sponge Calyx CE podatypa have been reported incorrectly. Synthetic studies and comparison with literature data have enabled the structures of these DKPs to be correctly reassigned. Evidence is presented to suggest that naturally occurring D-Pro-L-Xxx-DKPs are artifacts resulting from non-enzymatic epimerisation of the corresponding L-Pro-L-Xxx-DKP natural products.
引用
收藏
页码:2313 / 2320
页数:8
相关论文
共 73 条
  • [41] NMR ASSIGNMENTS, CONFORMATION, AND ABSOLUTE-CONFIGURATION OF DITRYPTOPHENALINE AND MODEL DIOXOPIPERAZINES
    MAES, CM
    POTGIETER, M
    STEYN, PS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06): : 861 - 866
  • [42] MODEL STUDIES OF COMPETING HYDROLYSIS AND EPIMERIZATION OF SOME TETRAPEPTIDES OF INTEREST IN AMINO-ACID RACEMIZATION STUDIES IN GEOCHRONOLOGY
    MOIR, ME
    CRAWFORD, RJ
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (11): : 2903 - 2913
  • [43] MURAO S, 1988, AGR BIOL CHEM TOKYO, V52, P885
  • [44] NUMATA A, 1994, J CHEM SOC P1, P1859
  • [45] OGURA H, 1975, CHEM PHARM BULL, V23, P2474
  • [46] STEREOSPECIFIC CYCLOLIZATION OF N-(ALPHA-HYDROXYACYL)-PHENYLALANYL-PROLINE LACTAMS
    OTT, H
    HOFMANN, A
    FREY, AJ
    [J]. TETRAHEDRON, 1963, 19 (11) : 1675 - &
  • [47] WIN-64821, A NOVEL NEUROKININ ANTAGONIST PRODUCED BY AN ASPERGILLUS SP .3. BIOSYNTHETIC ANALOGS
    POPP, JL
    MUSZA, LL
    BARROW, CJ
    RUDEWICZ, PJ
    HOUCK, DR
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (04) : 411 - 419
  • [48] BIOACTIVE CYCLIC DIPEPTIDES
    PRASAD, C
    [J]. PEPTIDES, 1995, 16 (01) : 151 - 164
  • [49] METABOLITES FROM THE MARINE SPONGE TEDANIA-IGNIS - A NEW ATISANEDIOL AND SEVERAL KNOWN DIKETOPIPERAZINES
    SCHMITZ, FJ
    VANDERAH, DJ
    HOLLENBEAK, KH
    ENWALL, CEL
    GOPICHAND, Y
    SENGUPTA, PK
    HOSSAIN, MB
    VANDERHELM, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 3941 - 3945
  • [50] SCHOLLKOPF U, 1988, LIEBIGS ANN CHEM, P1025