[6-13C]-(2S,4S)-5-chloroleucine:: synthesis and incubation studies with cultures of the cyanobacterium, Lyngbya majuscula

被引:16
作者
Gerwick, WH
Leslie, P
Long, GC
Marquez, BL
Willis, CL
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(02)02572-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[6-C-13]-(2S,4S)-5-Chloroleucine 12 was prepared in six steps and 26% overall yield from protected L-glutamic acid using (CH3I)-C-13 as the source of isotopic label. On feeding 12 to cultures of L. majuscula no incorporation of isotopic label into the trichlorinated marine natural product barbamide as detected. The synthesis of a novel dichloro amino acid 16 is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:285 / 288
页数:4
相关论文
共 28 条
  • [1] Vanadium haloperoxidases
    Butler, A
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (02) : 279 - 285
  • [2] MARINE HALOPEROXIDASES
    BUTLER, A
    WALKER, JV
    [J]. CHEMICAL REVIEWS, 1993, 93 (05) : 1937 - 1944
  • [3] The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit
    Chang, ZX
    Flatt, P
    Gerwick, WH
    Nguyen, VA
    Willis, CL
    Sherman, DH
    [J]. GENE, 2002, 296 (1-2) : 235 - 247
  • [4] NOVEL SPONGE DERIVED AMINO-ACIDS .17. A NOVEL CHLORINATED KETIDE AMINO-ACID, HERBAMIDE-A, FROM THE MARINE SPONGE DYSIDEA-HERBACEA
    CLARK, WD
    CREWS, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1185 - 1188
  • [5] Regioselective lipase-catalyzed synthesis of L-glutamic alpha-monoamide derivatives. Effect of the N-blocking group
    Conde, S
    LopezSerrano, P
    Fierros, M
    Biezma, MI
    Martinez, A
    RodriguezFranco, MI
    [J]. TETRAHEDRON, 1997, 53 (34) : 11745 - 11752
  • [6] COREY EJ, 1972, TETRAHEDRON LETT, P3769
  • [7] DAKIN HD, 1946, J BIOL CHEM, V164, P615
  • [8] NOVEL PRODUCTS DERIVED FROM UNPRECEDENTED TRANSFORMATIONS OF 3,3,3-TRIALKYNYLPROPIONALDEHYDE DERIVATIVES
    FELDMAN, KS
    WEINREB, CK
    YOUNGS, WJ
    BRADSHAW, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 1213 - 1215
  • [9] A new diketopiperazine derivative from the South China Sea sponge Dysidea fragilis
    Fu, X
    Zeng, LM
    Su, JY
    Pais, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07): : 695 - 696
  • [10] New diketopiperazines from the sponge Dysidea chlorea
    Fu, X
    Ferreira, MLG
    Schmitz, FJ
    Kelly-Borges, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10): : 1226 - 1231