Synthesis, structure and biological activity of alpha-trifluoromethyl-substituted thyreotropin releasing hormone

被引：11

作者：

Koksch, B ^{[1
]}

Ullmann, D ^{[1
]}

Jakubke, HD ^{[1
]}

Burger, K ^{[1
]}

机构：

[1] UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1996年 / 80卷 / 01期

关键词：

alpha-trifluoromethyl-substituted amino acids; TRH; proteolytic stability; NMR spectroscopy; IR spectroscopy;

D O I：

10.1016/S0022-1139(96)03461-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The incorporation of alpha-trifluoromethyl pyroglutamic acid into thyreotropin releasing hormone TRH, results in the complete stability of the pGlu-His bond against proteolytic degradation by pyroglutamyl aminopeptidase II. The influence of the trifluoromethyl group on structure and receptor affinity has been studied.

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页码：53 / 57

页数：5

相关论文

共 12 条

[1] REGULATION AND CELLULAR-LOCALIZATION OF THE MEMBRANE-BOUND THYROTROPIN-RELEASING HORMONE-DEGRADING ENZYME IN PRIMARY CULTURES OF NEURONAL, GLIAL AND ADENOHYPOPHYSEAL CELLS [J].

BAUER, K ;

CARMELIET, P ;

SCHULZ, M ;

BAES, M ;

DENEF, C .

ENDOCRINOLOGY, 1990, 127 (03) :1224-1233

[2] SPECIFICITY OF A SERUM PEPTIDASE HYDROLYZING THYROLIBERIN AT THE PYROGLUTAMYL-HISTIDINE BOND [J].

BAUER, K ;

NOWAK, P ;

KLEINKAUF, H .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1981, 118 (01) :173-176

[3]

BURGER K, 1989, CHEM ZTG, V113, P243

[4]

BURGER K, 1990, CHEM ZTG, V114, P101

[5] PROTEASE-CATALYZED AND CHEMICAL PEPTIDE-BOND FORMATION WITH ALPHA-TRIFLUOROMETHYL SUBSTITUTED ALPHA-AMINO-ACIDS [J].

BURGER, K ;

MUTZE, K ;

HOLLWECK, W ;

KOKSCH, B ;

KUHL, P ;

JAKUBKE, HD ;

RIEDE, J ;

SCHIER, A .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (04) :321-331

[6] ORIENTATION RESTRICTIONS OF PEPTIDE HORMONE, THYROTROPIN-RELEASING FACTOR, DUE TO INTRAMOLECULAR HYDROGEN-BONDING [J].

GRANT, G ;

VALE, W ;

LING, N ;

RIVIER, J .

BIOCHEMISTRY, 1972, 11 (16) :3070-&

[7]

Konig W., 1993, PEPTIDE PROTEIN HORM

[8] MODULATION OF THE BIOLOGICAL-ACTIVITY OF THYROTROPIN-RELEASING-HORMONE BY ALTERNATE PROCESSING OF PRO-TRH [J].

LADRAM, A ;

BULANT, M ;

DELFOUR, A ;

MONTAGNE, JJ ;

VAUDRY, H ;

NICOLAS, P .

BIOCHIMIE, 1994, 76 (3-4) :320-328

[9]

Metcalf G., 1989, ANN NY ACAD SCI, P1

[10] REACTIONS OF TRIFLUOROMETHYL KETONES .9. INVESTIGATION OF THE STERIC EFFECT OF A TRIFLUOROMETHYL GROUP BASED ON THE STEREOCHEMISTRY ON THE DEHYDRATION OF TRIFLUOROMETHYL HOMOALLYL ALCOHOLS [J].

NAGAI, T ;

NISHIOKA, G ;

KOYAMA, M ;

ANDO, A ;

MIKI, T ;

KUMADAKI, I .

JOURNAL OF FLUORINE CHEMISTRY, 1992, 57 (1-3) :229-237