Picomole scale stereochemical analysis of sphingosines and dihydrosphingosines

被引:32
作者
Kawamura, A
Berova, N
Dirsch, V
Mangoni, A
Nakanishi, K
Schwartz, G
Bielawska, A
Hannun, Y
Kitagawa, I
机构
[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027
[2] MEM SLOAN KETTERING CANC CTR,NEW YORK,NY 10021
[3] DUKE UNIV,MED CTR,DEPT MED & CELL BIOL,DURHAM,NC 27710
[4] OSAKA UNIV,FAC PHARMACEUT SCI,DEPT PHARMACOL,SUITA,OSAKA 565,JAPAN
关键词
D O I
10.1016/0968-0896(96)00092-2
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
We have developed a simple picomole (low nanogram) scale HPLC scheme which can separate all eight isomers of sphingosine and dihydrosphingosine thus leading to the identification of their relative and absolute configurations. The amino group of the sample is derivatized to its fluorescent N-naphthimide which is analyzed by normal and chiral phase HPLC, coupled with fluorescence peak detection. If necessary, the results of this HPLC method can be further corroborated by measurements of circular dichroic (CD) spectra of the N-naphthimido-derivatives and/or N,O-chromophoric derivatives. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1035 / 1043
页数:9
相关论文
共 26 条
[1]  
BUEHRER BM, 1992, J BIOL CHEM, V267, P3154
[2]  
CARTER HE, 1947, J BIOL CHEM, V170, P285
[3]  
CARTER HE, 1951, J BIOL CHEM, V191, P727
[4]   SYNTHESIS OF ERYTHRO-ALPHA-BETA-HYDROXYSTEARIC ACID AND THREO-ALPHA-AMINO-BETA-HYDROXYSTEARIC ACIDS [J].
CARTER, HE ;
HARRISON, JB ;
SHAPIRO, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (19) :4705-4709
[5]  
CHAO R, 1992, J BIOL CHEM, V267, P23459
[6]   A 2-STEP CHEMICAL AND CIRCULAR DICHROIC METHOD FOR ASSIGNING THE ABSOLUTE-CONFIGURATIONS OF SPHINGOSINES [J].
DIRSCH, V ;
FREDERICO, J ;
ZHAO, N ;
CAI, GL ;
CHEN, YQ ;
VUNNAM, S ;
ODINGO, J ;
PU, H ;
NAKANISHI, K ;
BEROVA, N ;
LIOTTA, D ;
BIELAWSKA, A ;
HANNUN, Y .
TETRAHEDRON LETTERS, 1995, 36 (28) :4959-4962
[7]   ABSOLUTE CONFIGURATION OF SPHINGOSINE BASES [J].
GIGG, RH .
CHEMISTRY AND PHYSICS OF LIPIDS, 1969, 3 (01) :106-&
[8]   FUNCTIONS OF SPHINGOLIPIDS AND SPHINGOLIPID BREAKDOWN PRODUCTS IN CELLULAR-REGULATION [J].
HANNUN, YA ;
BELL, RM .
SCIENCE, 1989, 243 (4890) :500-507
[9]  
HANNUN YA, 1992, ALFRED BENZON SYMP S, V33, P257
[10]  
Harada N., 1983, CIRCULAR DICHROIC SP