Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study

被引:12
作者
Bose, PK [1 ]
Polavarapu, PL [1 ]
机构
[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA
基金
美国国家科学基金会;
关键词
carbohydrates; monosaccharides; pentaacetates; vibrational circular dichroism; infrared spectra; vibrational spectra; circular dichroism;
D O I
10.1016/S0008-6215(99)00211-6
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
Vibrational absorption and circular dichroism spectra of five different monosaccharide pentaacetates were measured. These spectra were found to be dominated by the contributions from the acetate groups. In the carbonyl region, alpha- and beta-D-glucose pentaacetates do not show measurable vibrational circular dichroism (VCD), but alpha- and beta-D-galactose pentaacetates and alpha-D-mannose pentaacetate show significant VCD, with mannose pentaacetate giving opposite signs to those of alpha- and beta-D-galactose pentaacetates. These observed features are interpreted to reflect the orientation of carbonyl groups around the carbohydrate ring. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:135 / 141
页数:7
相关论文
共 29 条
[1]   FOURIER-TRANSFORM INFRARED, VIBRATIONAL CIRCULAR-DICHROISM OF SUGARS - A SPECTRA-STRUCTURE CORRELATION [J].
BACK, DM ;
POLAVARAPU, PL .
CARBOHYDRATE RESEARCH, 1984, 133 (01) :163-167
[2]  
Barron L.D., 1982, Molecular Light Scattering and Optical Activity
[3]   VIBRATIONAL RAMAN OPTICAL-ACTIVITY OF CARBOHYDRATES [J].
BARRON, LD ;
GARGARO, AR ;
WEN, ZQ .
CARBOHYDRATE RESEARCH, 1991, 210 :39-49
[4]   VIBRATIONAL RAMAN OPTICAL-ACTIVITY OF CYCLODEXTRINS [J].
BARRON, LD ;
GARGARO, AR ;
WEN, ZQ ;
MACNICOL, DD ;
BUTTERS, C .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :513-516
[5]   VIBRATIONAL CIRCULAR-DICHROISM OF PROTEINS IN H2O SOLUTION [J].
BAUMRUK, V ;
KEIDERLING, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6939-6942
[6]   VIBRATIONAL RAMAN OPTICAL-ACTIVITY STUDY OF D-GLUCOSE [J].
BELL, AF ;
BARRON, LD ;
HECHT, L .
CARBOHYDRATE RESEARCH, 1994, 257 (01) :11-24
[7]   Polysaccharide vibrational Raman optical activity: Laminarin and pullulan [J].
Bell, AF ;
Hecht, L ;
Barron, LD .
JOURNAL OF RAMAN SPECTROSCOPY, 1995, 26 (12) :1071-1074
[8]   VIBRATIONAL RAMAN OPTICAL-ACTIVITY OF KETOSE MONOSACCHARIDES [J].
BELL, AF ;
HECHT, L ;
BARRON, LD .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1995, 51 (08) :1367-1378
[9]   LOW-WAVE-NUMBER VIBRATIONAL RAMAN OPTICAL-ACTIVITY OF CARBOHYDRATES [J].
BELL, AF ;
HECHT, L ;
BARRON, LD .
JOURNAL OF RAMAN SPECTROSCOPY, 1993, 24 (09) :633-635
[10]   DISACCHARIDE SOLUTION STEREOCHEMISTRY FROM VIBRATIONAL RAMAN OPTICAL-ACTIVITY [J].
BELL, AF ;
HECHT, L ;
BARRON, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5155-5161