Investigation of the synthetic route to pepstatin analogues by SPPS using O-protected and O-unprotected statine as building blocks

被引：7

作者：

Cadicamo, Cosimo D. ^{[1
]}

Asante, Vivian ^{[1
]}

Abu Ammar, Morhaf ^{[1
]}

Borelli, Claudia ^{[2
]}

Korting, Hans C. ^{[2
]}

Koksch, Beate ^{[1
]}

机构：

[1] FU Berlin, Dept Organ Chem, D-14195 Berlin, Germany

[2] Univ Munich, Dept Dermatol & Allergy, D-80337 Munich, Germany

来源：

JOURNAL OF PEPTIDE SCIENCE | 2009年 / 15卷 / 04期

关键词：

pepstatin A; O-silylation; SPPS; N-Fmoc-O-TBS-statine; STEREOSPECIFIC SYNTHESIS; ASPARTIC PROTEINASES; TETRAMIC ACIDS; INHIBITORS; PEPSIN; PENICILLOPEPSIN; DERIVATIVES; PEPTIDES; PROTEASE; RENIN;

D O I：

10.1002/psc.1111

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthetic route to pepstatin derivatives by a solid phase peptide synthesis using either O-protected or O-unprotected statine as a building block has been investigated. Statine was prepared according to a modified literature procedure, whereas protection of its 3-hydroxyl moiety using tert-butyldimethylsilylchloride (TEISCI) provided the novel O-TBS-protected statine building block. The O-tert-butyldimethylsilyl (TBS)-protected statine approach provides an improved synthetic strategy for the preparation of statine-containing peptides as demonstrated by the synthesis of the pepstatin analogue iva-Val-Leu-Sta-Ala-Sta. Copyright (C) 2009 European Peptide Society and John Wiley & Sons, Ltd.

引用

页码：272 / 277

页数：6

共 19 条

[1] RENIN INHIBITORS - SYNTHESES OF SUBNANOMOLAR, COMPETITIVE, TRANSITION-STATE ANALOG INHIBITORS CONTAINING A NOVEL ANALOG OF STATINE [J].

BOGER, J ;

PAYNE, LS ;

PERLOW, DS ;

LOHR, NS ;

POE, M ;

BLAINE, EH ;

ULM, EH ;

SCHORN, TW ;

LAMONT, BI ;

LIN, TY ;

KAWAI, M ;

RICH, DH ;

VEBER, DF .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (12) :1779-1790

[2] 3-DIMENSIONAL STRUCTURE OF THE COMPLEX OF THE RHIZOPUS-CHINENSIS CARBOXYL PROTEINASE AND PEPSTATIN AT 2.5-A RESOLUTION [J].

BOTT, R ;

SUBRAMANIAN, E ;

DAVIES, DR .

BIOCHEMISTRY, 1982, 21 (26) :6956-6962

[3] Aspartic proteinases in disease: A structural perspective [J].

Cooper, JB .

CURRENT DRUG TARGETS, 2002, 3 (02) :155-173

[4] SYNTHESIS OF CHIRAL URETHANE N-ALKOXYCARBONYL TETRAMIC ACIDS FROM URETHANE N-CARBOXYANHYDRIDES (UNCAS) [J].

FEHRENTZ, JA ;

BOURDEL, E ;

CALIFANO, JC ;

CHALOIN, O ;

DEVIN, C ;

GARROUSTE, P ;

LIMALEITE, AC ;

LLINARES, M ;

RIEUNIER, F ;

VIZAVONNA, J ;

WINTERNITZ, F ;

LOFFET, A ;

MARTINEZ, J .

TETRAHEDRON LETTERS, 1994, 35 (10) :1557-1560

[5] DIASTEREOFACIAL SELECTIVITY IN REDUCTION OF CHIRAL TETRAMIC ACIDS [J].

GALEOTTI, N ;

PONCET, J ;

CHICHE, L ;

JOUIN, P .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5370-5376

[6] Design of potent inhibitors for human brain memapsin 2 (β-secretase) [J].

Ghosh, AK ;

Shin, DW ;

Downs, D ;

Koelsch, G ;

Lin, XL ;

Ermolieff, J ;

Tang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3522-3523

[7] An accurate method for the quantitation of Fmoc-derivatized solid phase supports [J].

Gude, M ;

Ryf, J ;

White, PD .

LETTERS IN PEPTIDE SCIENCE, 2002, 9 (4-5) :203-206

[8] CONFORMATIONAL FLEXIBILITY IN THE ACTIVE-SITES OF ASPARTYL PROTEINASES REVEALED BY A PEPSTATIN FRAGMENT BINDING TO PENICILLOPEPSIN [J].

JAMES, MNG ;

SIELECKI, A ;

SALITURO, F ;

RICH, DH ;

HOFMANN, T .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1982, 79 (20) :6137-6141

[9] STEREOSPECIFIC SYNTHESIS OF N-PROTECTED STATINE AND ITS ANALOGS VIA CHIRAL TETRAMIC ACID [J].

JOUIN, P ;

CASTRO, B ;

NISATO, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (06) :1177-1182

[10] SYNTHESIS OF THE NOVEL PI-(BENZYLOXYMETHYL)-PROTECTED HISTIDINE ANALOG OF STATINE - INHIBITION OF PENICILLOPEPSIN BY PEPSTATIN-DERIVED PEPTIDES CONTAINING DIFFERENT STATINE SIDE-CHAIN DERIVATIVES [J].

MAIBAUM, J ;

RICH, DH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1571-1576

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