Biomimetic seleninates and selenonates

被引：55

作者：

Abdo, Mohannad ^{[1
]}

Knapp, Spencer ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 29期

关键词：

D O I：

10.1021/ja8034448

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a variety of pyranose, nucleoside-, (amino acid)-, and polyhydric-based seleninic and selenonic acids by DMDO oxidation of the corresponding selenoesters is reported, as well as some unusual coupling reactions of the seleninate and selenonate functionality with biological nucleophilic groups (sulfhydryl, indole, phenol, imidazole. carboxamide) that are found in proteins and enzyme active sites.

引用

页码：9234 / +

页数：3

共 26 条

[1] Boronic acids as inhibitors of steroid sulfatase [J].

Ahmed, Vanessa ;

Liu, Yong ;

Silvestro, Cassandra ;

Taylor, Scott D. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8564-8573

[2] THE METATHESIS OF N-SILYLAMINES AND BENZENESELENENYL CHLORIDE - AN EFFICIENT SELENENAMIDE SYNTHESIS [J].

BACK, TG ;

KERR, RG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (02) :308-310

[3] REACTIONS OF SULFONHYDRAZIDES WITH BENZENESELENINIC ACID, SELENIUM HALIDES, AND SULFUR HALIDES - A CONVENIENT PREPARATION OF SELENOSULFONATES AND THIOSULFONATES [J].

BACK, TG ;

COLLINS, S ;

KRISHNA, MV .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01) :38-42

[4] A CONVENIENT SYNTHESIS OF SELENOLSULFONATES FROM THE OXIDATION OF SULFONHYDRAZIDES WITH BENZENESELENINIC ACID [J].

BACK, TG ;

COLLINS, S .

TETRAHEDRON LETTERS, 1980, 21 (23) :2213-2214

[5] Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/insulin-like growth factor II receptor [J].

Berkowitz, DB ;

Maiti, G ;

Charette, BD ;

Dreis, CD ;

MacDonald, RG .

ORGANIC LETTERS, 2004, 6 (26) :4921-4924

[6] Potassium alkaneselenonates and other alkyl derivatives of selenium [J].

Bird, ML ;

Challenger, F .

JOURNAL OF THE CHEMICAL SOCIETY, 1942, :570-574

[7] Allium chemistry:: Synthesis, natural occurrence, biological activity, and chemistry of Se-alk(en)ylselenocysteines and their γ-glutamyl derivatives and oxidation products [J].

Block, E ;

Birringer, M ;

Jiang, WQ ;

Nakahodo, T ;

Thompson, HJ ;

Toscano, PJ ;

Uzar, H ;

Zhang, X ;

Zhu, ZJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (01) :458-470

[8] REACTION OF TRYPTOPHAN DERIVATIVES WITH PHENYLSULFENYL CHLORIDE AND PHENYLSELENENYL BROMIDE [J].

CRICH, D ;

DAVIES, JW .

TETRAHEDRON LETTERS, 1989, 30 (32) :4307-4308

[9] PERFLUORO-ORGANOCHALCOGENYL ACIDS IN HIGH OXIDATION-STATES [J].

HAAS, A ;

HERKT, S .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 71 (02) :165-166

[10] OXIDATION-REDUCTION REACTIONS OF ORGANOSELENIUM COMPOUNDS .1. MECHANISM OF REACTION BETWEEN SELENINIC ACIDS AND THIOLS [J].

KICE, JL ;

LEE, TWS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (16) :5094-5102

← 1 2 3 →