SUBSTITUENT EFFECTS ON THE PH-INDEPENDENT HYDROLYSIS OF 2'-SUBSTITUTED NICOTINAMIDE ARABINOSIDES

被引：24

作者：

HANDLON, AL ^{[1
]}

OPPENHEIMER, NJ ^{[1
]}

机构：

[1] UNIV CALIF SAN FRANCISCO,DEPT PHARMACEUT CHEM,SAN FRANCISCO,CA 94143

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 17期

关键词：

D O I：

10.1021/jo00017a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rates of the pH-independent hydrolysis of a series of 2'-substituted nicotinamide arabinosides have been measured and are used to analyze the direct inductive substituent effect on the stability of oxocarbocationic intermediates.

引用

页码：5009 / 5010

页数：2

共 18 条

[1] BULL HG, 1978, J BIOL CHEM, V253, P5186
[2] MECHANISM IN CARBOHYDRATE CHEMISTRY
CAPON, B
[J]. CHEMICAL REVIEWS, 1969, 69 (04) : 407 - +
[3] DEFINITION OF INDUCTIVE SUBSTITUENT CONSTANTS
CHARTON, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) : 1222 - &
[4] COLOWICK SP, 1951, J BIOL CHEM, V191, P447
[5] RE-EXAMINATION OF INDUCTIVE SUBSTITUENT CONSTANTS DERIVED FROM PKA VALUES OF 4-SUBSTITUTED QUINUCLIDINES - POLAR EFFECTS .8.
GROB, CA
SCHAUB, B
SCHLAGETER, MG
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (01) : 57 - 62
[6] INDUCTIVITY AND BRIDGING IN CARBOCATIONS
GROB, CA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (12) : 426 - 431
[7] HINE J, 1975, STRUCTURAL EFFECTS E, P97
[8] PYRIDINE-NUCLEOTIDE CHEMISTRY - A NEW MECHANISM FOR THE HYDROXIDE-CATALYZED HYDROLYSIS OF THE NICOTINAMIDE GLYCOSYL BOND
JOHNSON, RW
MARSCHNER, TM
OPPENHEIMER, NJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2257 - 2263
[9] PYRIDINE COENZYME ANALOGS - SYNTHESIS AND CHARACTERIZATION OF ALPHA-NICOTINAMIDE AND BETA-NICOTINAMIDE ARABINOSIDE ADENINE DINUCLEOTIDES
KAM, BL
MALVER, O
MARSCHNER, TM
OPPENHEIMER, NJ
[J]. BIOCHEMISTRY, 1987, 26 (12) : 3453 - 3461
[10] THE EVALUATION OF INDUCTIVE AND RESONANCE EFFECTS ON REACTIVITY .1. HYDROLYSIS RATES OF ACETALS OF NON-CONJUGATED ALDEHYDES AND KETONES
KREEVOY, MM
TAFT, RW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (21) : 5590 - 5595

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