Efficient synthesis of enantiopure β-amino-γ-keto acids from L-homoserine

被引:10
作者
Sharma, AK [1 ]
Hergenrother, PJ [1 ]
机构
[1] Univ Illinois, Roger Adams Lab, Dept Chem, Urbana, IL 61801 USA
关键词
D O I
10.1021/ol0345327
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A variety of beta-amino-gamma-keto acids were prepared in four steps from commercially available L-homoserine. The reaction sequence is highlighted by a Ni-catalyzed Grignard addition to a N-protected derivative Of L-homoserine. One of the beta-amino-gamma-keto acids was then used to create a beta-peptide trimer composed solely of beta-amino-gamma-keto acids.
引用
收藏
页码:2107 / 2109
页数:3
相关论文
共 27 条
[1]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[2]   TOTAL CHEMICAL SYNTHESIS OF A UNIQUE TRANSCRIPTION FACTOR-RELATED PROTEIN - CMYC-MAX [J].
CANNE, LE ;
FERREDAMARE, AR ;
BURLEY, SK ;
KENT, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :2998-3007
[3]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[4]   Site-specific protein modification using a ketone handle [J].
Cornish, VW ;
Hahn, KM ;
Schultz, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8150-8151
[5]   A designed phenylalanyl-tRNA synthetase variant allows efficient in vivo incorporation of aryl ketone functionality into proteins [J].
Datta, D ;
Wang, P ;
Carrico, IS ;
Mayo, SL ;
Tirrell, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5652-5653
[6]   ONE-STEP SYNTHESIS OF KETONES FROM CARBOXYLIC-ACIDS AND GRIGNARD-REAGENTS IN THE PRESENCE OF A NICKEL(II)-PHOSPHINE CATALYST [J].
FIANDANESE, V ;
MARCHESE, G ;
RONZINI, L .
TETRAHEDRON LETTERS, 1983, 24 (34) :3677-3680
[7]   Peptide folding induces high and selective affinity of a linear and small β-peptide to the human somatostatin receptor 4 [J].
Gademann, K ;
Kimmerlin, T ;
Hoyer, D ;
Seebach, D .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (15) :2460-2468
[8]   Can one derive the conformational preference of a β-peptide from its CD spectrum? [J].
Glättli, A ;
Daura, X ;
Seebach, D ;
van Gunsteren, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :12972-12978
[9]   De novo design of antibacterial β-peptides [J].
Hamuro, Y ;
Schneider, JP ;
DeGrado, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12200-12201
[10]  
Juaristi E, 1999, CURR MED CHEM, V6, P983