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
收藏
页码:3131 / 3137
页数:7
相关论文
共 60 条
[41]  
Paulmier C., 1986, SELENIUM REAGENTS IN
[42]   Internally stabilized selenocysteine derivatives:: syntheses, 77Se NMR and biomimetic studies [J].
Phadnis, PP ;
Mugesh, G .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (13) :2476-2481
[43]   SELENIUM - BIOCHEMICAL ROLE AS A COMPONENT OF GLUTATHIONE PEROXIDASE [J].
ROTRUCK, JT ;
POPE, AL ;
GANTHER, HE ;
SWANSON, AB ;
HAFEMAN, DG ;
HOEKSTRA, WG .
SCIENCE, 1973, 179 (4073) :588-590
[44]   OPTICALLY ACTIVE SELENIUM-CONTAINING AMINO ACIDS - SYNTHESIS OF L-SELENOCYSTINE AND L-SELENOLANTIONINE [J].
ROY, J ;
GORDON, W ;
SCHWARTZ, IL ;
WALTER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (02) :510-&
[45]  
Sakai M, 1997, HETEROCYCLES, V44, P319
[46]   Stereoselective synthesis of Boc-protected L-seleno- and tellurolanthionine, L-seleno- and tellurocystine and derivatives [J].
Schneider, A ;
Rodrigues, OED ;
Paixao, MW ;
Appelt, HR ;
Braga, AL ;
Wessjohann, LA .
TETRAHEDRON LETTERS, 2006, 47 (06) :1019-1021
[47]   Influence of pH and flanking serine on the redox potential of S-S and S-Se bridges of Cys-Cys and Cys-Sec peptides [J].
Schneider, Alex ;
Brandt, Wolfgang ;
Wessjohann, Ludger A. .
BIOLOGICAL CHEMISTRY, 2007, 388 (10) :1099-1101
[48]   Organocatalytic asymmetric aldol reactions mediated by a cysteine-derived prolinamide [J].
Schwab, Ricardo S. ;
Galetto, Fabio Z. ;
Azeredo, Juliano B. ;
Braga, Antonio L. ;
Luedtke, Diogo S. ;
Paixao, Marcio W. .
TETRAHEDRON LETTERS, 2008, 49 (34) :5094-5097
[49]   Modular synthesis of chiral N-protected β-seleno amines and amides via cleavage of 2-oxazolidinones and application in palladium-catalyzed asymmetric allylic alkylation [J].
Sehnem, Jasquer A. ;
Vargas, Fabricio ;
Milani, Priscila ;
Nascimento, Vanessa ;
Braga, Antonio L. .
SYNTHESIS-STUTTGART, 2008, 8 (08) :1262-1268
[50]   Synthesis of Se- and Te-containing amino acids: Useful probes for structural studies of proteins. [J].
Silks, LA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 136 :611-616