[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 [J].
Butler, A .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (02) :279-285
[2]   MARINE HALOPEROXIDASES [J].
BUTLER, A ;
WALKER, JV .
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 [J].
Chang, ZX ;
Flatt, P ;
Gerwick, WH ;
Nguyen, VA ;
Willis, CL ;
Sherman, DH .
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 [J].
CLARK, WD ;
CREWS, P .
TETRAHEDRON LETTERS, 1995, 36 (08) :1185-1188
[5]   Regioselective lipase-catalyzed synthesis of L-glutamic alpha-monoamide derivatives. Effect of the N-blocking group [J].
Conde, S ;
LopezSerrano, P ;
Fierros, M ;
Biezma, MI ;
Martinez, A ;
RodriguezFranco, MI .
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 [J].
FELDMAN, KS ;
WEINREB, CK ;
YOUNGS, WJ ;
BRADSHAW, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :1213-1215
[9]   A new diketopiperazine derivative from the South China Sea sponge Dysidea fragilis [J].
Fu, X ;
Zeng, LM ;
Su, JY ;
Pais, M .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :695-696
[10]   New diketopiperazines from the sponge Dysidea chlorea [J].
Fu, X ;
Ferreira, MLG ;
Schmitz, FJ ;
Kelly-Borges, M .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10) :1226-1231