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Hydrolysis of N-phenylacetyl-a-methyl-alpha-amino acids by benzylpenicillinacylase.

作者信息

Rossi D, Calcagni A

出版信息

Experientia. 1985 Jan 15;41(1):35-7. doi: 10.1007/BF02005859.

DOI:10.1007/BF02005859
PMID:3881272
Abstract

Enzymatic hydrolysis of several racemic N-phenylacetyl-alpha-methyl-alpha-amino acids containing an additional aliphatic, aromatic or polar substitutent on the chiral carbon atom, has been studied by using benzylpenicillinacylase from Escherichia coli A.T.C.C.9637. Both the rate of hydrolysis and the stereoselectivity were found to be considerably lower than in the case of natural alpha-amino acids. Steric and electronic factors in the side chains influencing the stereoselectivity are discussed. Key words. Benzylpenicillinacylase; enzymatic hydrolysis; alpha-methyl-alpha-amino acids.

摘要

相似文献

1
Hydrolysis of N-phenylacetyl-a-methyl-alpha-amino acids by benzylpenicillinacylase.
Experientia. 1985 Jan 15;41(1):35-7. doi: 10.1007/BF02005859.
2
[Study of penicillin amidase for E. coli. Kinetics of enzymatic hydrolysis of 7-phenylacetamidodeacetoxycephalosporanic acid].[大肠杆菌青霉素酰胺酶的研究。7-苯乙酰氨基去乙酰氧基头孢烷酸的酶促水解动力学]
Antibiotiki. 1976 Aug;21(8):698-704.
3
Substrate specificity of penicillin acylase of E. coli.大肠杆菌青霉素酰化酶的底物特异性
J Antibiot (Tokyo). 1978 Aug;31(8):783-8. doi: 10.7164/antibiotics.31.783.
4
Penicillinamidohydrolase in Escherichia coli. I. Substrate specificity.大肠杆菌中的青霉素酰胺水解酶。I. 底物特异性。
Folia Microbiol (Praha). 1975;20(3):224-30. doi: 10.1007/BF02876783.
5
Deacylation of acylamino compounds other than penicillins by the cell-bound penicillin acylase of Escherichia coli.大肠杆菌细胞结合青霉素酰化酶对除青霉素外的酰基氨基化合物的脱酰作用。
Biochem J. 1969 Dec;115(4):741-5. doi: 10.1042/bj1150741.
6
Substrate specificity of penicillin amidase from E. coli.大肠杆菌青霉素酰胺酶的底物特异性
Biochim Biophys Acta. 1980 Dec 4;616(2):283-9. doi: 10.1016/0005-2744(80)90145-x.
7
[E. coli penicillin amidase. Methods for estimating the close ionization constants of ionogenic groups of the enzyme complex with substrates containing free amino groups].[大肠杆菌青霉素酰胺酶。估算酶与含游离氨基底物形成的复合物中离子基团的紧密电离常数的方法]
Antibiotiki. 1981 Dec;26(12):920-32.
8
Application of an immobilized penicillin acylase to the deprotection of N-phenylacetyl insulin.固定化青霉素酰化酶在N-苯乙酰胰岛素脱保护中的应用。
Biopolymers. 1986;25 Suppl:S109-14.
9
[Penicillin amidase from E. coli. The kinetic and equilibrium parameters of the enzymatic hydrolysis of 7-phenylacetamidodesacetoxycephalosporanic acid catalyzed by an immobile enzyme].[来自大肠杆菌的青霉素酰胺酶。固定化酶催化7-苯乙酰氨基去乙酰氧基头孢烷酸酶促水解的动力学和平衡参数]
Antibiotiki. 1980 Nov;25(11):808-15.
10
Alteration of the catalytic efficiency of penicillin amidase from Escherichia coli.大肠杆菌青霉素酰胺酶催化效率的改变。
Appl Environ Microbiol. 1989 Oct;55(10):2556-60. doi: 10.1128/aem.55.10.2556-2560.1989.

本文引用的文献

1
The preparation of optically active alpha-C-substituted glutamic acid.光学活性α-C-取代谷氨酸的制备。
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Studies on optically active amino acids. XV. Studies on alpha-alkyl-alpha-amino acids. 8. Absolute configuration of optically active alpha-methylserine and 2-amino-2-methyl-3-butenoic acid.旋光性氨基酸的研究。十五。α-烷基-α-氨基酸的研究。8. 旋光性α-甲基丝氨酸和2-氨基-2-甲基-3-丁烯酸的绝对构型。
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Studies on optically active amino acids. XIV. Studies on alpha-alkyl-alpha-amino acids. VII. Determination of absolute configuration of optically active alpha-methylphenylglycine and 1-methyl-1-phenylpropylamine.
旋光性氨基酸的研究。十四。α-烷基-α-氨基酸的研究。七。旋光性α-甲基苯甘氨酸和1-甲基-1-苯丙胺绝对构型的测定。
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[Circular dichroism and configuration of alpha-amine acids].[α-氨基酸的圆二色性与构型]
Pharmazie. 1970 May-Jun;25(5):336-40.
5
Use of Escherichia coli A.T.C.C. 9637 for the asymmetric hydrolysis of amino acid derivatives.利用大肠杆菌美国典型培养物保藏中心9637号菌株进行氨基酸衍生物的不对称水解。
Experientia. 1965 Jun 15;21(6):317-8. doi: 10.1007/BF02144688.
6
Studies with alpha-methyl amino acids. Resolution and amino protection.α-甲基氨基酸的研究。拆分与氨基保护。
J Org Chem. 1975 Apr 4;40(7):953-5. doi: 10.1021/jo00895a032.