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

来源：

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS | 2000年 / 270卷 / 02期

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

[1] CLIONAMIDE, A MAJOR METABOLITE OF THE SPONGE CLIONA-CELATA GRANT [J].

ANDERSEN, RJ ;

STONARD, RJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (17) :2325-2328

[2] HALOCYAMINES - NOVEL ANTIMICROBIAL TETRAPEPTIDE-LIKE SUBSTANCES ISOLATED FROM THE HEMOCYTES OF THE SOLITARY ASCIDIAN HALOCYNTHIA-RORETZI [J].

AZUMI, K ;

YOKOSAWA, H ;

ISHII, S .

BIOCHEMISTRY, 1990, 29 (01) :159-165

[3] STRUCTURE OF THE TUNICHROME OF TUNICATES AND ITS ROLE IN CONCENTRATING VANADIUM [J].

BAYER, E ;

SCHIEFER, G ;

WAIDELICH, D ;

SCIPPA, S ;

DEVICENTIIS, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (01) :52-54

[4] INVIVO INCORPORATION OF C-14 PHENYLALANINE INTO ASCIDIAN TUNICHROME [J].

HE, X ;

KUSTIN, K ;

PARRY, DL ;

ROBINSON, WE ;

RUBERTO, G ;

NAKANISHI, K .

EXPERIENTIA, 1992, 48 (04) :367-371

[5] THE TUNICHROMES - A CLASS OF REDUCING BLOOD PIGMENTS FROM SEA SQUIRTS - ISOLATION, STRUCTURES, AND VANADIUM CHEMISTRY [J].

OLTZ, EM ;

BRUENING, RC ;

SMITH, MJ ;

KUSTIN, K ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6162-6172

[6] Celenamide E, a tripeptide alkaloid from the Patagonian sponge Cliona chilensis [J].

Palermo, JA ;

Brasco, MFR ;

Cabezas, E ;

Balzaretti, V ;

Seldes, AM .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (04) :488-490

[7] C-14- and H-3-tyrosine incorporation into Ascidia ceratodes tunichrome in vivo [J].

Robinson, WE ;

Kustin, K ;

Matulef, K ;

Parry, DL ;

He, XY ;

Ryan, EK .

COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1996, 115 (04) :475-481

[8] ALPHA,BETA-DEHYDRO-3,4-DIHYDROXYPHENYLALANINE DERIVATIVES - POTENTIAL SCHLEROTIZATION INTERMEDIATES IN NATURAL COMPOSITE-MATERIALS [J].

RZEPECKI, LM ;

NAGAFUCHI, T ;

WAITE, JH .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1991, 285 (01) :17-26

[9] ALPHA,BETA-DEHYDRO-3,4-DIHYDROXYPHENYLALANINE DERIVATIVES - RATE AND MECHANISM OF FORMATION [J].

RZEPECKI, LM ;

WAITE, JH .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1991, 285 (01) :27-36

[10] LINEAR PEPTIDE ALKALOIDS FROM THE SPONGE CLIONA-CELATA (GRANT) CELENAMIDES-C AND CELENAMIDE-D [J].

STONARD, RJ ;

ANDERSEN, RJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (20) :2121-2126