Straightforward Method for the Synthesis of Selenocysteine and Selenocystine Derivatives from L-Serine Methyl Ester

被引：19

作者：

Braga, Antonio L. ^{[1
]}

Wessjohann, Ludger A. ^{[2
]}

Taube, Paulo S. ^{[1
]}

Galetto, Fabio Z. ^{[1
,3
]}

de Andrade, Fabiano M. ^{[3
]}

机构：

[1] Univ Fed Santa Catarina, Dept Quim, BR-88040970 Florianopolis, SC, Brazil

[2] Leibniz Inst Plant Biochem, D-06120 Halle, Germany

[3] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2010年 / 18期

关键词：

organoselenium; selenoamino acids; selenocysteine; selenocystine; tellurocysteine; CONTAINING AMINO-ACIDS; RING-OPENING REACTION; BETA-SELENO AMIDES; EFFICIENT SYNTHESIS; ORGANOSELENIUM; THIOREDOXIN; CHEMISTRY; SULFUR; SE; PHENYLSELENOALANINE;

D O I：

10.1055/s-0030-1258188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A set of selenoamino acids has been efficiently synthesized under smooth conditions by a simple, flexible and modular strategy. In this method, O-mesylated L-serine methyl ester is generated in situ and directly substituted with various selenolate anions to afford selenocysteine, selenolanthionine, and selenocystine derivatives in good yields. Also, a tellurocysteine derivative can be obtained by this method.

引用

页码：3131 / 3137

页数：7

共 60 条

[1] Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx-Like Activity [J].

Alberto, Eduardo E. ;

Soares, Letiere C. ;

Sudati, Jessie H. ;

Borges, Antonio C. A. ;

Rocha, Joao B. T. ;

Braga, Antonio. L. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (25) :4211-4214

[2] Physiological functions of thioredoxin and thioredoxin reductase [J].

Arnér, ESJ ;

Holmgren, A .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 2000, 267 (20) :6102-6109

[3] Function of thioredoxin reductase as a peroxynitrite reductase using selenocystine or ebselen [J].

Arteel, GE ;

Briviba, K ;

Sies, H .

CHEMICAL RESEARCH IN TOXICOLOGY, 1999, 12 (03) :264-269

[4] Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form [J].

Baig, R. B. Nasir ;

Sudhir, V. Sai ;

Chandrasekaran, Srinivasan .

TETRAHEDRON-ASYMMETRY, 2008, 19 (12) :1425-1429

[5] Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms [J].

Battin, Erin E. ;

Brumaghim, Julia L. .

CELL BIOCHEMISTRY AND BIOPHYSICS, 2009, 55 (01) :1-23

[6] TYPE-I IODOTHYRONINE DEIODINASE IS A SELENOCYSTEINE-CONTAINING ENZYME [J].

BERRY, MJ ;

BANU, L ;

LARSEN, PR .

NATURE, 1991, 349 (6308) :438-440

[7] The redox potential of selenocystine in unconstrained cyclic peptides [J].

Besse, D ;

Siedler, F ;

Diercks, T ;

Kessler, H ;

Moroder, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (08) :883-885

[8] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].

Braga, AL ;

Paixao, MW ;

LUdtke, DS ;

Silveira, CC ;

Rodrigues, OED .

ORGANIC LETTERS, 2003, 5 (15) :2635-2638

[9] Efficient synthesis of chiral β-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation [J].

Braga, AL ;

Vargas, F ;

Sehnem, JA ;

Braga, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :9021-9024

[10] Straightforward synthesis of non-natural selenium containing amino acid derivatives and peptides [J].

Braga, AL ;

Lüdtke, DS ;

Paixao, MW ;

Alberto, EE ;

Stefani, HA ;

Juliano, L .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4260-4264

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