Pseudo-A(1,3) strain as a key conformational control element in the design of poly-L-proline type II peptide mimics

被引：47

作者：

Zhang, R ^{[1
]}

Brownewell, F ^{[1
]}

Madalengoitia, JS ^{[1
]}

机构：

[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 16期

关键词：

D O I：

10.1021/ja972494e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A strategy for the synthesis of peptide mimics of the poly-L-proline type II secondary structure from 4-substituted prolines is presented. Dimeric and trimeric oligomers composed of 3-substituted prolines are shown by NMR to preferentially populate the poly-L-proline type II secondary structure in both CDCl3 and D2O. Oligomers composed of 4-substituted prolines thus imitate the desired backbone conformation and are able to incorporate non-prolyl side chains on the proline backbone.

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页码：3894 / 3902

页数：9

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共 22 条

[11] ANGIOTENSIN-CONVERTING ENZYME-INHIBITORS - MERCAPTAN, CARBOXYALKYL DIPEPTIDE, AND PHOSPHINIC ACID INHIBITORS INCORPORATING 4-SUBSTITUTED PROLINES [J].

KRAPCHO, J ;

TURK, C ;

CUSHMAN, DW ;

POWELL, JR ;

DEFORREST, JM ;

SPITZMILLER, ER ;

KARANEWSKY, DS ;

DUGGAN, M ;

ROVNYAK, G ;

SCHWARTZ, J ;

NATARAJAN, S ;

GODFREY, JD ;

RYONO, DE ;

NEUBECK, R ;

ATWAL, KS ;

PETRILLO, EW .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1148-1160

[12] Crystal structure of the conserved core of HIV-1 Nef complexed with a Src family SH3 domain [J].

Lee, CH ;

Saksela, K ;

Mirza, UA ;

Chait, BT ;

Kuriyan, J .

CELL, 1996, 85 (06) :931-942

[13] VARIATIONS IN THE TURN-FORMING CHARACTERISTICS OF N-ACYL PROLINE UNITS [J].

LIANG, GB ;

RITO, CJ ;

GELLMAN, SH .

BIOPOLYMERS, 1992, 32 (03) :293-301

[14] Molecular mechanics parameters and conformational free energies of proline-containing peptides [J].

McDonald, DQ ;

Still, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1385-1391

[15] DEVELOPMENT OF A MODEL FOR THE DELTA-OPIOID RECEPTOR PHARMACOPHORE .1. CONFORMATIONALLY RESTRICTED TYR(1) REPLACEMENTS IN THE CYCLIC DELTA-RECEPTOR SELECTIVE TETRAPEPTIDE TYR-C[D-CYS-PHE-D-PEN]OH (JOM-13) [J].

MOSBERG, HI ;

LOMIZE, AL ;

WANG, CG ;

KROONA, H ;

HEYL, DL ;

SOBCZYKKOJIRO, K ;

MA, WL ;

MOUSIGIAN, C ;

PORRECA, F .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (25) :4371-4383

[16] HIGHLY CHEMOSELECTIVE REDUCTION OF N-BOC PROTECTED LACTAMS [J].

PEDREGAL, C ;

EZQUERRA, J ;

ESCRIBANO, A ;

CARRENO, MC ;

RUANO, JLG .

TETRAHEDRON LETTERS, 1994, 35 (13) :2053-2056

[17] Delineation of an active fragment and poly(L-proline) II conformation for candidacidal activity of bactenecin 5 [J].

Raj, PA ;

Marcus, E ;

Edgerton, M .

BIOCHEMISTRY, 1996, 35 (14) :4314-4325

[18] THE IMPORTANCE OF EXTENDED CONFORMATIONS AND, IN PARTICULAR, THE P-II CONFORMATION FOR THE MOLECULAR RECOGNITION OF PEPTIDES [J].

SILIGARDI, G ;

DRAKE, AF .

BIOPOLYMERS, 1995, 37 (04) :281-292

[19] CONVERSION OF L-PYROGLUTAMIC ACID TO 4-ALKYL-SUBSTITUTED L-PROLINES - THE SYNTHESIS OF TRANS-4-CYCLOHEXYL-L-PROLINE [J].

THOTTATHIL, JK ;

MONIOT, JL ;

MUELLER, RH ;

WONG, MKY ;

KISSICK, TP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3140-3143

[20] STRUCTURAL BASIS FOR THE BINDING OF PROLINE-RICH PEPTIDES TO SH3 DOMAINS [J].

YU, HT ;

CHEN, JK ;

FENG, SB ;

DALGARNO, DC ;

BRAUER, AW ;

SCHREIBER, SL .

CELL, 1994, 76 (05) :933-945