Methyl- and (trifluoromethyl)alkene peptide isosteres:: Synthesis and evaluation of their potential as β-turn promoters and peptide mimetics

被引:145
作者
Wipf, P [1 ]
Henninger, TC [1 ]
Geib, SJ [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/jo981057v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:6088 / 6089
页数:2
相关论文
共 25 条
[1]   FLUORINE-CONTAINING ORGANOZINC REAGENTS .6. THE PREPARATION OF ALPHA-TRIFLUOROMETHYL-ALPHA-BETA-UNSATURATED CARBOXYLIC-ACID ESTERS [J].
ALLMENDINGER, T ;
LANG, RW .
TETRAHEDRON LETTERS, 1991, 32 (03) :339-340
[2]   FLUOROALKENES AS PEPTIDE ISOSTERES - GROUND-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].
BARTLETT, PA ;
OTAKE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3107-3111
[3]   BETA-TURNS IN PROTEINS [J].
CHOU, PY ;
FASMAN, GD .
JOURNAL OF MOLECULAR BIOLOGY, 1977, 115 (02) :135-175
[4]   ALLYLSILANES IN ORGANIC-SYNTHESIS - STEREOSELECTIVE SYNTHESIS OF TRANS-ALKENE PEPTIDE ISOSTERES [J].
DALY, MJ ;
WARD, RA ;
THOMPSON, DF ;
PROCTER, G .
TETRAHEDRON LETTERS, 1995, 36 (41) :7545-7548
[5]   The gamma-methyl-E-olefin as isosteric replacement of the peptide bond [J].
Devadder, S ;
Verheyden, P ;
Jaspers, HCM ;
VanBinst, G ;
Tourwe, D .
TETRAHEDRON LETTERS, 1996, 37 (05) :703-706
[6]   AMIDE BOND REPLACEMENTS INCORPORATED INTO CCK-B SELECTIVE DIPEPTOIDS [J].
FINCHAM, CI ;
HIGGINBOTTOM, M ;
HILL, DR ;
HORWELL, DC ;
OTOOLE, JC ;
RATCLIFFE, GS ;
REES, DC ;
ROBERTS, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) :1472-1484
[7]   EFFICIENT CARBONYL ADDITION OF POLYFLUOROCHLOROETHYL, POLYFLUOROCHLOROETHYLIDENE, AND POLYFLUOROCHLOROETHENYL UNITS BY MEANS OF 1,1,1-TRICHLORO-2,2,2-TRIFLUOROETHANE AND ZINC [J].
FUJITA, M ;
HIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (12) :4377-4384
[8]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[9]   AN ACHIRAL DIPEPTIDE MIMETIC THAT PROMOTES BETA-HAIRPIN FORMATION [J].
GARDNER, RR ;
LIANG, GB ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3280-3281
[10]  
]Hoegberg T., 1987, J ORG CHEM, V52, P2033