Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

被引:54
作者
Agarkov, A
Greenfield, S
Xie, DJ
Pawlick, R
Starkey, G
Gilbertson, SR
机构
[1] Univ Texas, Med Branch, Chem Biol Program, Galveston, TX 77555 USA
[2] Washington Univ, Dept Chem, St Louis, MO 63130 USA
关键词
catalysis; phosphine; rhodium; palladium;
D O I
10.1002/bip.20395
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
Combinatorial chemistry has recently burst on the scene as a valuable tool for the discovery of new drug candidates. The ability to synthesize hundreds of compounds for screening is a useful complement to rational drug design. There are many similarities between the design of new therapeutic agents and the development of new asymmetric ligands, the most important of which is the limitation of a rational design strategy. For this reason a program was begun that would allow the use of combinatorial technology in the development of new ligands for transition metal catalyzed asymmetric reactions. Because of the large number of catalytic reactions they are involved in the system was based around phosphine ligands. This paper reports the synthesis of phosphine derivatives of alanine, proline, and the aromatic amino acids tyrosine and hydroxyphenylglycine. Examples of the use of these amino acids in the synthesis of peptides possessing helical and beta-turn secondary structures are presented. Metal complexes of these peptide-based ligands are used in hydrogenation and alkylation reactions. (C) 2005 Wiley Periodicals, Inc.
引用
收藏
页码:48 / 73
页数:26
相关论文
共 54 条
[1]   DIMETHYL SULFOXIDE-ACID ANHYDRIDE MIXTURES FOR OXIDATION OF ALCOHOLS [J].
ALBRIGHT, JD ;
GOLDMAN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2416-&
[2]  
[Anonymous], 1972, ORGANIC PHOSPHORUS C
[3]   BETA-I-TURN AND BETA-II-TURN CONFORMATIONS IN MODEL DIPEPTIDES WITH THE PRO-XAA SEQUENCES [J].
AUBRY, A ;
CUNG, MT ;
MARRAUD, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7640-7647
[4]   REACTIONS OF ELEMENTAL SULFUR .2. THE REACTION OF ALKALI CYANIDES WITH SULFUR, AND SOME SINGLE-SULFUR TRANSFER REACTIONS [J].
BARTLETT, PD ;
DAVIS, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (10) :2513-2516
[5]   ADDITION OF DIPHENYLPHOSPHINE TO MICHAEL-TYPE OLEFINS - THE PREPARATION OF PHOSPHINE-NITRILE AND PHOSPHINE-ESTER LIGANDS [J].
BLINN, DA ;
BUTTON, RS ;
FARAZI, V ;
NEEB, MK ;
TAPLEY, CL ;
TREHEARNE, TE ;
WEST, SD ;
KRUGER, TL ;
STORHOFF, BN .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 393 (01) :143-152
[6]  
Bodanszky M., 1984, PRACTICE PEPTIDE SYN
[7]  
Boudier A, 2000, CHEM-EUR J, V6, P2748, DOI 10.1002/1521-3765(20000804)6:15<2748::AID-CHEM2748>3.0.CO
[8]  
2-Q
[9]   SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].
CAI, DW ;
PAYACK, JF ;
BENDER, DR ;
HUGHES, DL ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181
[10]   A β-peptide reverse turn that promotes hairpin formation [J].
Chung, YJ ;
Christianson, LA ;
Stanger, HE ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (40) :10555-10556