Model systems for flavoenzyme activity. A versatile synthesis of N(3)-alkylated flavins

被引：9

作者：

Dutra, JK ^{[1
]}

Cuello, AO ^{[1
]}

Rotello, VM ^{[1
]}

机构：

[1] UNIV MASSACHUSETTS,DEPT CHEM,AMHERST,MA 01003

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 23期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(97)00819-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of isoalloxazines (flavins) with primary and secondary alcohols using Mitsunobu conditions provides flavins alkylated at the N(3) position. This method provides a versatile and divergent synthesis of both primary alkyl flavins, and the difficult to synthesize secondary alkyl flavins. (C) 1997 Elsevier Science Ltd.

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页码：4003 / 4004

页数：2

相关论文

共 12 条

[1] Model systems for flavoenzyme activity. Modulation of flavin redox potentials through π-stacking interactions [J].

Breinlinger, EC ;

Rotello, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :1165-1166

[2]

Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]

[3] STEREOSPECIFIC AND STEREOSELECTIVE REACTIONS .1. PREPARATION OF AMINES FROM ALCOHOLS [J].

MITSUNOB.O ;

WADA, M ;

SANO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :679-&

[4] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[5]

MULLER F, 1991, CHEM BIOCH FLAVOENZY, V1, P4

[6] Model systems for flavoenzyme activity: One- and two-electron reduction of flavins in aprotic hydrophobic environments [J].

Niemz, A ;

Imbriglio, J ;

Rotello, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :887-892

[7]

RIVLIN R, 1991, CHEM BIOCH FLAVOENZY, V1, P201

[8]

SEWARD EM, 1987, J AM CHEM SOC, V102, P1783

[9] COENZYME MODELS .37. A CROWN ETHER FLAVIN MIMIC - SYNTHESIS AND PROPERTIES OF A FLAVIN BEARING A CROWN RING AS A RECOGNITION SITE [J].

SHINKAI, S ;

ISHIKAWA, Y ;

SHINKAI, H ;

TSUNO, T ;

MAKISHIMA, H ;

UEDA, K ;

MANABE, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1801-1808

[10] FLAVIN COENZYMES - AT THE CROSSROADS OF BIOLOGICAL REDOX CHEMISTRY [J].

WALSH, C .

ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (05) :148-155