The kapakahines, cyclic peptides from the marine sponge Cribrochalina olemda

被引:86
作者
Yeung, BKS
Nakao, Y
Kinnel, RB
Carney, JR
Yoshida, WY
Scheuer, PJ
KellyBorges, M
机构
[1] UNIV HAWAII MANOA,DEPT CHEM,HONOLULU,HI 96822
[2] HARBOR BRANCH OCEANOG INST INC,FT PIERCE,FL 34936
关键词
D O I
10.1021/jo960725e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four cyclic peptides, kapakahines A-D, were isolated from the marine sponge Cribrochalina olemda. Their structures including complete stereochemistry were elucidated by spectral analysis and chemical degradation. The unique structural feature of these peptides is the lack of an amide linkage between two tryptophan residues. Instead the ring is closed by a bond from the indole nitrogen of Trp-1 to the beta-carbon of Trp-2.
引用
收藏
页码:7168 / 7173
页数:6
相关论文
共 15 条
[1]   STRUCTURE ELUCIDATION OF THE ANTIBIOTIC DESERTOMYCIN THROUGH THE USE OF NEW TWO-DIMENSIONAL NMR TECHNIQUES [J].
BAX, A ;
ASZALOS, A ;
DINYA, Z ;
SUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8056-8063
[3]   STRUCTURE DETERMINATION OF A TETRASACCHARIDE - TRANSIENT NUCLEAR OVERHAUSER EFFECTS IN THE ROTATING FRAME [J].
BOTHNERBY, AA ;
STEPHENS, RL ;
LEE, JM ;
WARREN, CD ;
JEANLOZ, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :811-813
[4]   MARINE ALKALOIDS .3. BROMO-SUBSTITUTED ALKALOIDS FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA, FLUSTRAMINE-C AND FLUSTRAMINOL-A AND FLUSTRAMINOL-B [J].
CARLE, JS ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (17) :3440-3443
[5]   MARINE ALKALOIDS .15. 2 ALKALOIDS, FLUSTRAMINE-E AND DEBROMOFLUSTRAMINE-B, FROM THE MARINE BRYOZOAN FLUSTRA-FOLIACEA [J].
HOLST, PB ;
ANTHONI, U ;
CHRISTOPHERSEN, C ;
NIELSEN, PH .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (07) :997-1000
[6]   TUMOR INHIBITORS .82. BRUCEANTIN, A NEW POTENT ANTILEUKEMIC SIMAROUBOLIDE FROM BRUCEA-ANTIDYSENTERICA [J].
KUPCHAN, SM ;
BRITTON, RW ;
ZIEGLER, MF ;
SIGEL, CW .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :178-179
[7]   DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE [J].
MARFEY, P .
CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) :591-596
[8]   KAPAKAHINE-B - A CYCLIC HEXAPEPTIDE WITH AN ALPHA-CARBOLINE RING-SYSTEM FROM THE MARINE SPONGE CRIBROCHALINA-OLEMDA [J].
NAKAO, Y ;
YEUNG, BKS ;
YOSHIDA, WY ;
SCHEUER, PJ ;
KELLYBORGES, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8271-8272
[9]  
PIHLAJA K, 1994, CARBON 13 NMR CHEM S, P325
[10]  
SANDERS JKM, 1987, MODERN NMR SPECTROSC, P226