Quantitative enzymatic protection of D-amino acid methyl esters by exploiting 'relaxed' enantioselectivity of penicillin-G amidase in organic solvent

被引：17
作者：
Carboni, C
Quaedflieg, PJLM
Broxterman, QB
Linda, P
Gardossi, L
机构：
[1] Univ Trieste, Dipartimento Sci Farmaceut, I-34127 Trieste, Italy
[2] DSM Res & Patents, Life Sci Adv Synth, Catalysis & Dev, NL-6160 MD Geleen, Netherlands
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 52期
关键词：
D-amino acids; penicillin-G amidase; protection of amino groups; organic solvent; biocatalysis;
D O I：
10.1016/j.tetlet.2004.10.153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9649 / 9652
页数：4
相关论文
共 26 条
[1]   Computational analysis of the aminic subsite of PGA explains the influence of amine structure on enantioselectivity [J].
Basso, A ;
Braiuca, P ;
Clementi, S ;
Ebert, C ;
Gardossi, L ;
Linda, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2002, 19 :423-430
[2]  
Basso A, 2001, CROAT CHEM ACTA, V74, P757
[3]   Activity of covalently immobilised PGA in water miscible solvents at controlled aw [J].
Basso, A ;
De Martin, L ;
Ebert, C ;
Gardossi, L ;
Linda, P ;
Zlatev, V .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :851-855
[4]   Selectivity of penicillin G acylase towards phenylacetic acid derivatives in amide bond synthesis in toluene [J].
Basso, A ;
De Martin, L ;
Ebert, C ;
Gardossi, L ;
Linda, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 16 (02) :73-80
[5]   D-Phenylglycine and D-4-hydroxyphenylglycine methyl esters via penicillin G acylase catalysed resolution in organic solvents [J].
Basso, A ;
Braiuca, P ;
De Martin, L ;
Ebert, C ;
Gardossi, L ;
Linda, P .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1789-1796
[6]  
BASSO A, 1999, J MOL CATAL B-ENZYM, V6, P437
[7]  
Bossi A, 1998, BIOTECHNOL BIOENG, V60, P454, DOI 10.1002/(SICI)1097-0290(19981120)60:4<454::AID-BIT7>3.0.CO
[8]  
2-L
[9]   A homology model of penicillin acylase from Alcaligenes faecalis and in silico evaluation of its selectivity [J].
Braiuca, P ;
Ebert, C ;
Fischer, L ;
Gardossi, L ;
Linda, P .
CHEMBIOCHEM, 2003, 4 (07) :615-622
[10]   PENICILLIN ACYLASE-CATALYZED PROTECTION AND DEPROTECTION OF AMINO-GROUPS AS A PROMISING APPROACH IN ENZYMATIC PEPTIDE-SYNTHESIS [J].
DIDZIAPETRIS, R ;
DRABNIG, B ;
SCHELLENBERGER, V ;
JAKUBKE, HD ;
SVEDAS, V .
FEBS LETTERS, 1991, 287 (1-2) :31-33
123