The solid phase synthesis of alpha,alpha-disubstituted unnatural amino acids and peptides (di-UPS)

被引:51
作者
Scott, WL [1 ]
Zhou, CY [1 ]
Fang, ZQ [1 ]
ODonnell, MJ [1 ]
机构
[1] INDIANA UNIV PURDUE UNIV, DEPT CHEM, INDIANAPOLIS, IN 46202 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)00715-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper reports a new, mild procedure (''di-UPS'') for the solid phase synthesis of racemic alpha,alpha-disubstituted amino acids (1) and epimeric alpha,alpha-disubstituted terminal amino acid residues (2, R-3=H) in a resin bound peptide. The synthetic route is compatible with most protected amino acid side chains and can be used in a continuing solid phase synthesis. DI-UPS should find wide applicability in the design and solid phase synthesis of hybrid amino acids and peptides, and the construction of basis units for combinatorial chemistry. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3695 / 3698
页数:4
相关论文
共 43 条
[1]   Self-addition products from the alkylation of amino acid-derived oxazolidinones: X-ray molecular structures of (2R,4S,1'S)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-benzyl-2-phenyl-1,3-oxazolidin-5-one, (2R,4S,1'S)- and (2R,4S,1'R)-3-benzoyl-4-[benzoylamino(phenyl)methyl]-4-isopropyl-2-phenyl-1,3-oxazolidin-5-one [J].
Abell, AD ;
Taylor, JM ;
Oldham, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (11) :1299-1304
[2]   Synthesis and derivatization of a versatile alpha-substituted lactam dipeptide isostere [J].
Acton, JJ ;
Jones, AB .
TETRAHEDRON LETTERS, 1996, 37 (25) :4319-4322
[3]  
Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289
[4]   ENANTIOMERICALLY ENRICHED ALPHA-METHYL AMINO-ACIDS - USE OF AN ACYCLIC, CHIRAL ALANINE-DERIVED DIANION WITH A HIGH DIASTEREOFACIAL BIAS [J].
BERKOWITZ, DB ;
SMITH, MK .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1233-1238
[5]   Optically active 3-amino-2H-azirines as synthons for enantiomerically pure alpha,alpha-disubstituted alpha-amino acids: Syntheses of isovaline synthons and a segment of Trichotoxin A-50 [J].
Bucher, CB ;
Heimgartner, H .
HELVETICA CHIMICA ACTA, 1996, 79 (07) :1903-1915
[6]   SUPRAMOLECULAR ASYMMETRIC INDUCTION - A NEW CONCEPT APPLIED TO THE SUPPORTED ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
CALMES, M ;
DAUNIS, J ;
ISMAILI, H ;
JACQUIER, R ;
KOUDOU, J ;
NKUSI, G ;
ZOUANATE, A .
TETRAHEDRON, 1990, 46 (17) :6021-6032
[7]   CHIRAL 2-CYANO ESTERS AS SYNTHETIC INTERMEDIATES IN THE SYNTHESIS OF R-ALPHA-METHYLVALINE AND S-ALPHA-METHYLVALINE [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA ;
LAPENA, Y .
TETRAHEDRON, 1995, 51 (20) :5921-5928
[8]  
CZARNIK A, 1996, ACC CHEM RES, V29
[9]   2-methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of alpha-methylphenylalanine and alpha-methyl-beta-phenylserine [J].
Davis, FA ;
Liu, H ;
Reddy, GV .
TETRAHEDRON LETTERS, 1996, 37 (31) :5473-5476
[10]  
Dorizon P, 1996, SYNLETT, P1071