CHEMICAL SYNTHESIS OF ALLYSINE ETHYLENE ACETAL AND CONVERSION IN-SITU INTO 1-PIPERIDEINE-6-CARBOXYLIC ACID - KEY INTERMEDIATE OF THE ALPHA-AMINOADIPIC ACID FOR BETA-LACTAM ANTIBIOTICS BIOSYNTHESIS

被引:24
作者
RUMBERO, A
MARTIN, JF
LUMBRERAS, MA
LIRAS, P
ESMAHAN, C
机构
[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN
[2] UNIV LEON,FAC BIOL,DEPT ECOL GENET & MICROBIOL,E-24071 LEON,SPAIN
关键词
D O I
10.1016/0968-0896(95)00110-3
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
Synthesis of alpha-amino acid allysine ethylene acetal from 3,4-dihydro-2H-pyran and its conversion in situ into 1-piperideine-6-carboxylic acid with an exceedingly simple work-up are described.
引用
收藏
页码:1237 / 1240
页数:4
相关论文
共 14 条
[1]  
ADLINGTON RM, 1990, MOLECULAR MECHANISMS IN BIOORGANIC PROCESSES, P1
[2]  
COPPOLA GM, 1984, SYNTHESIS-STUTTGART, P1021
[3]  
ENGLISH J, 1963, ORG SYNTHESES COLL, V4, P499
[4]   CATABOLISM OF L-LYSINE BY PSEUDOMONAS-AERUGINOSA [J].
FOTHERGILL, JC ;
GUEST, JR .
JOURNAL OF GENERAL MICROBIOLOGY, 1977, 99 (MAR) :139-155
[5]   QUANTITATIVE-DETERMINATION OF AMINO-ACIDS IN TISSUE-CULTURE CELLS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
KABUS, P ;
KOCH, G .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1982, 108 (02) :783-790
[6]   L-LYSINE EPSILON-AMINOTRANSFERASE INVOLVED IN CEPHAMYCIN-C SYNTHESIS IN STREPTOMYCES-LACTAMDURANS [J].
KERN, BA ;
HENDLIN, D ;
INAMINE, E .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1980, 17 (04) :679-685
[7]  
Martin J F, 1989, Adv Biochem Eng Biotechnol, V39, P153
[8]   AMINO GROUP BLOCKING - IMPROVED METHOD FOR N-PHTHALOYLATION USING N-(ETHOXYCARBONYL)PHTHALIMIDE [J].
MCARTHUR, CR ;
WORSTER, PM ;
OKON, AU .
SYNTHETIC COMMUNICATIONS, 1983, 13 (04) :311-318
[9]   CROSS-LINKING OF COLLAGEN AND ELASTIN - PROPERTIES OF LYSYL OXIDASE [J].
SIEGEL, RC ;
PINNELL, SR ;
MARTIN, GR .
BIOCHEMISTRY, 1970, 9 (23) :4486-&
[10]   REACTION OF ORTHO-PHTHALALDEHYDE AND THIOLS WITH PRIMARY AMINES - FORMATION OF 1-ALKYL(AND ARYL)THIO-2-ALKYLISOINDOLES [J].
SIMONS, SS ;
JOHNSON, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2886-2891