ASSESSMENT OF C-13-SHIFT PARAMETERS IN DI AND TRI-O-(3-NITROPROPANOYL)-D-GLUCOPYRANOSES

被引:11
作者
PFEFFER, PE [1 ]
VALENTINE, KM [1 ]
MOYER, BG [1 ]
GUSTINE, DL [1 ]
机构
[1] USDA,SEA,REG PASTURE RES LAB,UNIVERSITY PK,PA 16802
关键词
D O I
10.1016/S0008-6215(00)85470-1
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
Natural-abundance 13C-n.m.r. spectra of seven di- and tri-O-(3-nitropropanoyl)-α- and -β-d-glucopyranoses are reported and discussed. Linear regression-analysis of the extracted 13C-substituted parameters associated with esterification at various positions of the α- and β-glucose skeletons yielded two sets of substituent chemical-shift constants. The chemical shifts calculated from these generated parameters agreed well with the experimentally obtained values for each compound. Additivity of the substituent-induced shifts as a function of esterification site and substituent orientation is discussed. The structures of three previously uncharacterized di- and tri-esters were ascertained by using the parameters established. © 1979.
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页码:1 / 8
页数:8
相关论文
共 20 条
[1]   APPLICATIONS OF ARTIFICIAL INTELLIGENCE FOR CHEMICAL INFERENCE .11. ANALYSIS OF C-13 NUCLEAR MAGNETIC-RESONANCE DATA FOR STRUCTURE ELUCIDATION OF ACYCLIC AMINES [J].
CARHART, RE ;
DJERASSI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (13) :1753-1759
[2]   C-13 MAGNETIC-RESONANCE .23. METHYLDECALINS/LI [J].
DALLING, DK ;
GRANT, DM ;
PAUL, EG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3718-3724
[3]  
DORMAN DE, 1971, J AM CHEM SOC, V93, P4463, DOI 10.1021/ja00747a021
[4]  
DORMAN DE, 1970, J AM CHEM SOC, V92, P1355, DOI 10.1021/ja00708a040
[5]  
EGGART E, 1973, J AM CHEM SOC, V95, P3710
[6]   CARBON-13 MAGNETIC RESONANCE .2. CHEMICAL SHIFT DATA FOR ALKANES [J].
GRANT, DM ;
PAUL, EG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) :2984-+
[7]   ISOLATION OF NITRO-COMPOUNDS FROM ASTRAGALUS SPECIES [J].
HARLOW, MC ;
STERMITZ, FR ;
THOMAS, RD .
PHYTOCHEMISTRY, 1975, 14 (5-6) :1421-1423
[8]   C-13-NUCLEAR AND H-1-NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF PERMETHYLATED DISACCHARIDES [J].
HAVERKAMP, J ;
DEBIE, MJA ;
VLIEGENTHART, JF .
CARBOHYDRATE RESEARCH, 1974, 37 (01) :111-125
[9]   NITROPROPANYLGLUCOPYRANOSES IN CORONILLA-VARIA [J].
MAJAK, W ;
BOSE, RJ .
PHYTOCHEMISTRY, 1976, 15 (03) :415-417
[10]   THEORETICAL AND EMPIRICAL CALCULATIONS OF CARBON CHEMICAL-SHIFT IN TERMS OF ELECTRONIC DISTRIBUTION IN MOLECULES [J].
MARTIN, GJ ;
MARTIN, ML ;
ODIOT, S .
ORGANIC MAGNETIC RESONANCE, 1975, 7 (01) :2-17