CONTROL OF THE REGIOSELECTIVITY OF N-NUCLEOPHILE ADDITION TO N-CARBONYL PROTECTED DEHYDROALANINES - A MODEL FOR THE AMMONIA-LYASE ENZYMES

被引：16

作者：

GULZAR, MS ^{[1
]}

MORRIS, KB ^{[1
]}

GANI, D ^{[1
]}

机构：

[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 10期

关键词：

D O I：

10.1039/c39950001061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The regioselectivity of the addition of N-nucleophiles to N-carbonyl protected dehydroalanine derivatives, beta-conjugate addition vs. alpha-imine capture, can be controlled completely by varying the N-protecting group, or, the carboxy protecting group thereby providing a model for the chemistry of dehydroalanine residues within enzymes.

引用

页码：1061 / 1062

页数：2

共 9 条

[1] KINETICS AND MECHANISM OF SYN-ELIMINATION OF AMMONIA FROM (2S,3R)-3-METHYLASPARTIC ACID BY METHYLASPARTASE [J].

ARCHER, CH ;

GANI, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :140-142

[2]

BOTTING NP, 1992, SPECIAL PUBLICATION, V111, P95

[3] CLONING, SEQUENCING, AND EXPRESSION IN ESCHERICHIA-COLI OF THE CLOSTRIDIUM-TETANOMORPHUM GENE ENCODING BETA-METHYLASPARTASE AND CHARACTERIZATION OF THE RECOMBINANT PROTEIN [J].

GODA, SK ;

MINTON, NP ;

BOTTING, NP ;

GANI, D .

BIOCHEMISTRY, 1992, 31 (44) :10747-10756

[4] ENANTIOSPECIFIC CONJUGATE ADDITION OF N-NUCLEOPHILES TO SUBSTITUTED FUMARIC ACIDS USING METHYLASPARTASE [J].

GULZAR, MS ;

AKHTAR, M ;

GANI, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (13) :1601-1602

[5]

Hanson K. R., 1972, ENZYMES, V7, P75

[6] ASYMMETRIC-SYNTHESIS OF ALANINE BY CATALYTIC-HYDROGENATION OF CHIRAL N-ALPHA-ACETYLDEHYDROALANINAMIDES [J].

HARADA, K ;

TAKASAKI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (05) :1427-1428

[7] USE OF N-15 AND DEUTERIUM-ISOTOPE EFFECTS TO DETERMINE THE CHEMICAL MECHANISM OF PHENYLALANINE AMMONIA-LYASE [J].

HERMES, JD ;

WEISS, PM ;

CLELAND, WW .

BIOCHEMISTRY, 1985, 24 (12) :2959-2967

[8] IDENTIFICATION OF SERINE-143 AS THE MOST LIKELY PRECURSOR OF DEHYDROALANINE IN THE ACTIVE-SITE OF HISTIDINE AMMONIA-LYASE - A STUDY OF THE OVEREXPRESSED ENZYME BY SITE-DIRECTED MUTAGENESIS [J].

LANGER, M ;

RECK, G ;

REED, J ;

RETEY, J .

BIOCHEMISTRY, 1994, 33 (21) :6462-6467

[9] ISOUREA-MEDIATED PREPARATION OF DEHYDRO AMINO-ACIDS [J].

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :3131-3132

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