SOLID-PHASE SYNTHESIS OF PEPTIDE PARA-NITROANILIDES

被引:23
作者
BURDICK, DJ
STRUBLE, ME
BURNIER, JP
机构
[1] Department of Bioorganic Chemistry, Genentech Inc., South San Francisco, CA 94080
关键词
D O I
10.1016/S0040-4039(00)77632-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile synthesis of peptide para -nitroanilides was developed using a novel urethane linked para -aminoanilide resin 3 and solid phase peptide synthesis. Conversion of the resulting peptide para -aminoanilides to the corresponding peptide para -nitroanilides was achieved by oxidation with sodium perborate. With the exception of sequences containing methionine, tryptophan and cysteine, all amino acid residues can be used. A representative synthesis of the tetrapeptide para -nitroanilide succinyl-Ala-Ala-Pro-Arg-PNA is described.
引用
收藏
页码:2589 / 2592
页数:4
相关论文
共 15 条
[1]  
BOTT R, 1987, ACS SYM SER, V334, P139
[2]   INVESTIGATION OF THE SUBSTRATE-BINDING SITE OF HUMAN PLASMIN USING TRIPEPTIDYL-PARA-NITROANILIDE SUBSTRATES [J].
CSSZABO, G ;
POZSGAY, M ;
ELODI, P .
THROMBOSIS RESEARCH, 1980, 20 (02) :199-206
[3]   SENSITIVE NEW SUBSTRATE FOR CHYMOTRYPSIN [J].
DELMAR, EG ;
LARGMAN, C ;
BRODRICK, JW ;
GEOKAS, MC .
ANALYTICAL BIOCHEMISTRY, 1979, 99 (02) :316-320
[4]   PREPARATION AND PROPERTIES OF 2 NEW CHROMOGENIC SUBSTRATES OF TRYPSIN [J].
ERLANGER, BF ;
COHEN, W ;
KOKOWSKY, N .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1961, 95 (02) :271-&
[5]   PROBING STERIC AND HYDROPHOBIC EFFECTS ON ENZYME-SUBSTRATE INTERACTIONS BY PROTEIN ENGINEERING [J].
ESTELL, DA ;
GRAYCAR, TP ;
MILLER, JV ;
POWERS, DB ;
BURNIER, JP ;
NG, PG ;
WELLS, JA .
SCIENCE, 1986, 233 (4764) :659-663
[6]   MONITORING OF REACTIONS IN SOLID-PHASE PEPTIDE SYNTHESIS WITH PICRIC ACID [J].
GISIN, BF .
ANALYTICA CHIMICA ACTA, 1972, 58 (01) :248-&
[7]   AMINO-ACIDS AND PEPTIDES .6. SYNTHESIS OF MERRIFIELD RESIN ESTERS OF N-PROTECTED AMINO-ACIDS WITH AID OF HYDROGEN-BONDING [J].
HORIKI, K ;
IGANO, KI ;
INOUYE, K .
CHEMISTRY LETTERS, 1978, (02) :165-168
[8]   COLOR TEST FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN SOLID-PHASE SYNTHESIS OF PEPTIDES [J].
KAISER, E ;
COLESCOT.RL ;
BOSSINGE.CD ;
COOK, PI .
ANALYTICAL BIOCHEMISTRY, 1970, 34 (02) :595-&
[9]   SODIUM PERBORATE - A CHEAP AND EFFECTIVE REAGENT FOR THE OXIDATION OF ANILINES AND SULFIDES [J].
MCKILLOP, A ;
TARBIN, JA .
TETRAHEDRON LETTERS, 1983, 24 (14) :1505-1508
[10]   SOLID PHASE PEPTIDE SYNTHESIS .1. SYNTHESIS OF A TETRAPEPTIDE [J].
MERRIFIELD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2149-&