L-THREONINE ALDOLASE IN ORGANIC-SYNTHESIS - PREPARATION OF NOVEL BETA-HYDROXY-ALPHA-AMINO ACIDS

被引：82

作者：

VASSILEV, VP

UCHIYAMA, T

KAJIMOTO, T

WONG, CH

机构：

[1] INST PHYS & CHEM RES, FRONTIER RES PROGRAM, WAKO, SAITAMA 35101, JAPAN

[2] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 23期

关键词：

D O I：

10.1016/0040-4039(95)00720-W

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The L-threonine aldolase from Candida humicola was used in the synthesis of multifunctional beta-hydroxy-alpha-amino acids. Of many aldehydes with different substituents tested as substrates for reaction with glycine, benzyloxy- and alkoxy- aldehydes are found to be good substrates, providing a new synthetic route to alpha-amino-beta,omega-dihydroxy and alpha,omega-diamino-beta-hydroxy acids. The enzymatic reactions are not stereospecific regarding the new stereocenter formed at the beta-carbon, though they all give L-alpha-amino acids.

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页码：4081 / 4084

页数：4

相关论文

共 12 条

[1] REACTION OF GLYCOLALDEHYDE WITH PROTEINS - LATENT CROSSLINKING POTENTIAL OF ALPHA-HYDROXYALDEHYDES [J].

ACHARYA, AS ;

MANNING, JM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1983, 80 (12) :3590-3594

[2] RABBIT MUSCLE ALDOLASE AS A CATALYST IN ORGANIC-SYNTHESIS [J].

BEDNARSKI, MD ;

SIMON, ES ;

BISCHOFBERGER, N ;

FESSNER, WD ;

KIM, MJ ;

LEES, W ;

SAITO, T ;

WALDMANN, H ;

WHITESIDES, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :627-635

[3] GROWTH-RESPONSE TO 4-HYDROXY-L-THREONINE OF ESCHERICHIA-COLI MUTANTS BLOCKED IN VITAMIN-B6 BIOSYNTHESIS [J].

DREWKE, C ;

NOTHEIS, C ;

HANSEN, U ;

LEISTNER, E ;

HEMSCHEIDT, T ;

HILL, RE ;

SPENSER, ID .

FEBS LETTERS, 1993, 318 (02) :125-128

[4] STEREOSPECIFIC LYSIS OF A RANGE OF BETA-HYDROXY-ALPHA-AMINO ACIDS CATALYZED BY A NOVEL ALDOLASE FROM STREPTOMYCES-AMAKUSAENSIS [J].

HERBERT, RB ;

WILKINSON, B ;

ELLAMES, GJ ;

KUNEC, EK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :205-206

[5]

Hiranuma S, 1995, RIKEN REV, V8, P19

[6] 2-O-BENZYLGLYCERALDEHYDE - A SYNTHETIC BUILDING BLOCK AVAILABLE IN BOTH ENANTIOMERIC FORMS AND CONFIGURATIONALLY STABLE OWING TO RAPID OLIGOMERIZATION [J].

JAGER, V ;

WEHNER, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (04) :469-470

[7] THREONINE ALDOLASE FROM CANDIDA-HUMICOLA .2. PURIFICATION, CRYSTALLIZATION AND PROPERTIES [J].

KUMAGAI, H ;

YOSHIDA, H ;

YAMADA, H ;

NAGATE, T .

BIOCHIMICA ET BIOPHYSICA ACTA, 1972, 258 (03) :779-&

[8]

Nakazawa H., 1975, US patent, Patent No. [3871958 (A), 3871958, US 3871958]

[9] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF HYDROXYTHREONINE, A BIOSYNTHETIC PRECURSOR OF RHIZOBITOXINE IN PSEUDOMONAS [J].

PIRRUNG, MC ;

NUNN, DS ;

MCPHAIL, AT ;

MITCHELL, RE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) :2095-2098

[10] SYNTHESIS OF L-BETA-HYDROXYAMINOACIDS USING SERINE HYDROXYMETHYLTRANSFERASE [J].

SAEED, A ;

YOUNG, DW .

TETRAHEDRON, 1992, 48 (12) :2507-2514