Plicatamide: A lead to the biosynthetic origins of the tunichromes?

被引:22
作者
Tincu, JA
Craig, AG
Taylor, SW [1 ]
机构
[1] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA
[2] Salk Inst Biol Studies, Clayton Fdn Labs Peptide Biol, La Jolla, CA 92037 USA
基金
美国国家科学基金会;
关键词
ascidian; celenamide; DOPA protein; halocyamine; mass spectrometry; oxidative decarboxylation; tunichrome;
D O I
10.1006/bbrc.2000.2449
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
Plicatamide is a modified octapeptide from the ascidian Styela plicata having the structure Phe-Phe-His-Leu-His-Phe-His-decarboxy Delta DOPA (where decarboxy Delta DOPA = decarboxy- (E)-alpha,beta-dehydro-3,4-dihydroxyphenylalanine), Edman sequencing, tandem mass spectrometry, and proton NMR have been used to characterize 100 mu g of the compound. Plicatamide represents an important link between two classes of biomolecules: the tunichromes which share an oxidatively decarboxylated C-terminus and higher molecular weight DOPA-polypeptides. The 8-residue sequence provides the first opportunity to investigate the biosynthetic origins of the tunichrome family by molecular biological techniques. (C) 2000 Academic Press.
引用
收藏
页码:421 / 424
页数:4
相关论文
共 16 条
[11]   CELENAMIDE-A AND CELENAMIDE-B, LINEAR PEPTIDE ALKALOIDS FROM THE SPONGE CLIONA-CELATA [J].
STONARD, RJ ;
ANDERSEN, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (18) :3687-3691
[12]   Novel 3,4-Di- and 3,4,5-trihydroxyphenylalanine-containing polypeptides from the blood cells of the ascidians Ascidia ceratodes and Molgula manhattensis [J].
Taylor, SW ;
Ross, MM ;
Waite, JH .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1995, 324 (02) :228-240
[13]   Morulin Pm:: A modified polypeptide containing TOPA and 6-bromotryptophan from the morula cells of the ascidian, Phallusia mammillata [J].
Taylor, SW ;
Kammerer, B ;
Nicholson, GJ ;
Pusecker, K ;
Walk, T ;
Bayer, E ;
Scippa, S ;
de Vincentiis, M .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1997, 348 (02) :278-288
[14]   New perspectives in the chemistry and biochemistry of the tunichromes and related compounds [J].
Taylor, SW ;
Kammerer, B ;
Bayer, E .
CHEMICAL REVIEWS, 1997, 97 (01) :333-346
[15]   OXIDATION OF PEPTIDYL 3,4-DIHYDROXYPHENYLALANINE ANALOGS - IMPLICATIONS FOR THE BIOSYNTHESIS OF TUNICHROMES AND RELATED OLIGOPEPTIDES [J].
TAYLOR, SW ;
MOLINSKI, TF ;
RZEPECKI, LM ;
WAITE, JH .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (03) :918-922
[16]   THE PHYLOGENY AND CHEMICAL DIVERSITY OF QUINONE-TANNED GLUES AND VARNISHES [J].
WAITE, JH .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1990, 97 (01) :19-29