USE OF DIMETHYLFORMAMIDE SULFUR-TRIOXIDE COMPLEX AS A SULFATING AGENT OF TYROSINE

被引:27
作者
FUTAKI, S [1 ]
TAIKE, T [1 ]
YAGAMI, T [1 ]
OGAWA, T [1 ]
AKITA, T [1 ]
KITAGAWA, K [1 ]
机构
[1] UNIV TOKUSHIMA,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期
关键词
D O I
10.1039/p19900001739
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dimethylformamide-sulphur trioxide (DMF-SO3) complex was found to be more suitable for tyrosine sulphation than pyridine-sulphur trioxide (Pyr-SO3) complex, the most commonly used sulphur trioxide complex for sulphation. The work-up after sulphation using DMF-SO3 was also easier than with Pyr-SO3. The usefulness of DMF-SO3 complex was demonstrated through the synthesis of two tyrosine sulphate [Tyr(SO3H)]-containing peptides, leucine-enkephalin sulphate and leucosulfakinin-II.
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收藏
页码:1739 / 1744
页数:6
相关论文
共 31 条
[1]   N-HYDROXYSUCCINIMIDE ESTERS IN PEPTIDE SYNTHESIS [J].
ANDERSON, GW ;
ZIMMERMAN, JE ;
CALLAHAN, FM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (19) :3039-&
[2]   INHIBITION OF N-GLYCOSYLATION INDUCES TYROSINE SULFATION OF HYBRIDOMA IMMUNOGLOBULIN-G [J].
BAEUERLE, PA ;
HUTTNER, WB .
EMBO JOURNAL, 1984, 3 (10) :2209-2215
[3]   UNE NOUVELLE METHODE DE SYNTHESE PEPTIDIQUE [J].
BOISSONNAS, RA .
HELVETICA CHIMICA ACTA, 1951, 34 (03) :874-879
[4]   CHARACTERIZATION OF LAMPREY FIBRINOPEPTIDES [J].
DOOLITTL.RF .
BIOCHEMICAL JOURNAL, 1965, 94 (03) :742-+
[5]  
ERRICKSON BW, 1973, J AM CHEM SOC, V95, P3750
[6]  
FUJII N, 1988, CHEM PHARM BULL, V36, P3281
[7]  
FUJII N, 1986, CHEM PHARM BULL, V34, P846
[8]   SULFUR-TRIOXIDE THIOL - A NOVEL SYSTEM FOR THE REDUCTION OF METHIONINE SULFOXIDE [J].
FUTAKI, S ;
YAGAMI, T ;
TAIKE, T ;
AKITA, T ;
KITAGAWA, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :653-658
[9]   FACILE REDUCTION OF METHIONINE SULFOXIDE WITH SULFUR-TRIOXIDE THIOL SYSTEM [J].
FUTAKI, S ;
TAIKE, T ;
YAGAMI, T ;
AKITA, T ;
KITAGAWA, K .
TETRAHEDRON LETTERS, 1989, 30 (33) :4411-4412
[10]   PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].
HANESSIAN, S ;
LAVALLEE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977