A highly sensitive HPLC method to discriminate enantiomeric amino deoxy sugars based on the derivatization with (S)-(+)-TBMB carboxylic acid

被引:12
作者
Bai, C
Nishida, Y
Ohrui, H
Meguro, H
机构
[1] Dept. of Appl. Biological Chemistry, Faculty of Agriculture, Tohoku University, Sendai 981
关键词
D O I
10.1080/07328309608005440
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
A picomole determination of the absolute configurations of amino deoxy sugars was demonstrated through the derivatization at the anomeric carbon with a fluorescent chiral reagent, (S)-(+)-TBMB carboxylic acid, followed by the HPLC separations of the derived diastereomeric isomers. Anew chemical procedure was developed to convert amino deoxy sugars into per-NH,O-acetylated glycosyl chlorides prior to derivatization with the reagent.
引用
收藏
页码:217 / 230
页数:14
相关论文
共 16 条
[1]  
Brimacombe J.S., 1967, CARBOHYD RES, V3, P318
[2]  
CONCHIE J, 1963, METHODS CARBOHYDRATE, V2, P332
[3]  
CRAMER FD, 1962, METHODS CARBOHYDRATE, V1, P243
[4]   KANAMYCIN .4. THE STRUCTURE OF KANAMYCIN [J].
CRON, MJ ;
FARDIG, OB ;
JOHNSON, DL ;
WHITEHEAD, DF ;
HOOPER, IR ;
LEMIEUX, RU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (15) :4115-4115
[5]   CHIRAL SYNTHONS FOR THE TOTAL SYNTHESIS OF FLUORO AMINO-ACIDS AND FLUORO ANALOGS OF ANTIBIOTIC SUGARS [J].
FAGHIH, R ;
ESCRIBANO, FC ;
CASTILLON, S ;
GARCIA, J ;
LUKACS, G ;
OLESKER, A ;
THANG, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4558-4564
[6]  
Horton D., 1972, METHODS CARBOHYDR CH, V6, P282
[7]   STANNOUS TRIFLATE MEDIATED GLYCOSIDATIONS - A STEREOSELECTIVE SYNTHESIS OF 2-AMINO 2-DEOXY-BETA-D-GLUCOPYRANOSIDES DIRECTLY WITH THE NATURAL N-ACETYL PROTECTING GROUP [J].
LUBINEAU, A ;
GALLIC, JL ;
MALLERON, A .
TETRAHEDRON LETTERS, 1987, 28 (42) :5041-5044
[8]  
MAEDA K, 1968, TETRAHEDRON LETT, P1875
[9]   EXTENSION OF THE BETA-GAL1,1-TRANSFER TO N-ACETYL 5-THIO-GENTOSAMINE BY GALACTOSYLTRANSFERASE [J].
NISHIDA, Y ;
WIEMANN, T ;
THIEM, J .
TETRAHEDRON LETTERS, 1993, 34 (18) :2905-2906
[10]   SYNTHESIS OF (S)-(+)-2-TERT-BUTYL-2-METHYL-1,3-BENZODIOXOLE-4-CARBOXYLIC ACID - A NEW TYPE CHIRAL DERIVATION REAGENT FOR AMINES AND ALCOHOLS [J].
NISHIDA, Y ;
OHRUI, H ;
MEGURO, H .
TETRAHEDRON LETTERS, 1989, 30 (39) :5277-5280