ENANTIOSELECTIVE ACYLATION OF β-PHENYLALANINE ACID AND ITS DERIVATIVES CATALYZED BY PENICILLIN G ACYLASE FROM Alcaligenes faecalis

REFERENCES

• Spiteller , P. ; von Nussbaum , F. β-Amino Acids in Natural Products . In Enantioselective Synthesis of β-Amino Acids, , 2nd ed. ; Juaristi , E. , Soloshonok , V.A. , Eds.; Wiley-VCH , New York , NY , 2005 ; pp. 19 – 93 .
   Google Scholar
• Morita , H. ; Nagashima , S. ; Takeya , K. ; Itokawa , H. ; Staka , Y. Structures and Conformation of Antitumor Cyclic β-Peptides, Astin A, B and C, From Aster tataricus . Tetrahedron 1995 , 51 , 1121 – 1132 .
   Web of Science ®Google Scholar
• Nagano , Y. ; Ikedo , K. ; Fujishima , A. ; Izawa , M. ; Tsubotani , S. ; Nishimura , O. ; Fujino , M. Pyloricidins, Novel Anti-Helicobacter pylori Antibiotics Produced by Bacillus sp . J. Antibiot. 2001 , 54 , 934 – 947 .
   PubMed Web of Science ®Google Scholar
• Faulconbridge , S.J. ; Holt , K.E. ; Sevillano , L.G. ; Lock , C.J. ; Tiffin , P.D. ; Tremayne , N. ; Winter , S. Preparation of Enantiomerically Enriched Aromatic β-Amino Acids via Enzymatic Resolution . Tetrahedron Lett. 2000 , 41 , 2679 – 2681 .
   Web of Science ®Google Scholar
• Cohen , S.G. ; Weinstein , S.Y. Hydrolysis of D(-)-Ethyl-β-phenyl-β-hydroxypropionate and D(-)-Ethyl-β-phenyl-β-acetamidopropionate by α-Chymotrypsin . J. Am. Chem. Soc. 1964 , 86 , 725 – 728 .
   Web of Science ®Google Scholar
• Soloshonok , V.A. ; Fokina , N.A. ; Rybakova , A.V. ; Shishkina , I.P. ; Galushko , S.V. ; Sorochinsky , A.E. ; Kukhar , V.P. ; Savchenko , M.V. ; Švedas , V.K. Biocatalytic Approach to Enantiomerically Pure β-Amino Acids . Tetrahedron: Asymmetry 1995 , 6 , 1601 – 1610 .
   Web of Science ®Google Scholar
• Groeger , H. ; Trauthwein , H. ; Buchholz , S. ; Drauz , K. ; Sacherer , C. ; Godfrin , S. ; Werner , H. The First Aminoacylase-Catalyzed Enantioselective Synthesis of Aromatic β-Amino Acids . Org. Biomol. Chem. 2004 , 2 , 1977 – 1978 .
   PubMed Web of Science ®Google Scholar
• Makoto , H. ; Junichi , M. ; Tairo , H. ; Jun , S. ; Sakayu , S. ; Jun , O. β-Aryl-β-Amino Acid Amino Transferase From Variovorax sp. JH2 Is Useful for Enantioselective β-Phenylalanine Production . Biocatal. Agric. Biotechnol. 2012 , 1 , 253 – 258 .
   Google Scholar
• Shewale , J.G. ; Deshpande , B.S. ; Sudhakaran , V.K. ; Ambedkar , S.S. Penicillin Acylase: Applications and Potentials . Process Biochem. 1992 , 27 , 131 – 143 .
   Web of Science ®Google Scholar
• Bruggin , K. ; Roos , E.C. ; Devroom , E. Penicillin Acylase in the Industrial Production of β-Lactam Antibiotics . Org. Process Res. Dev. 1998 , 2 , 128 – 133 .
   Web of Science ®Google Scholar
• Khimiuk , A.Y. ; Korennykh , A.V. ; van Langen , L.M. ; van Rantwijk , F. Penicillin Acylase-Catalyzed Peptide Synthesis in Aqueous Medium: A Chemoenzymatic Route to Stereoisomerically Pure Diketopiperazines . Tetrahedron: Asymmetry 2003 , 14 , 3123 – 3128 .
   Web of Science ®Google Scholar
• Fadnavis , N.W. ; Sharfuddin , M. ; Vadivel , S.K. Resolution of Racemic 2-Amino-1-butanol With Immobilized Penicillin G Acylase. Tetrahedron: Asymmetry 1999, 10, 4495–4500.
   Web of Science ®Google Scholar
• Chilov , G.G. ; Moody , H.M. ; Boesten , W.H.J. ; Švedas , V.K. Resolution of (R, S)- Phenylglycinonitrile by Penicillin Acylase-Catalyzed Acylation in Aqueous Medium . Tetrahedron: Asymmetry 2003 , 14 , 2613 – 2617 .
   Web of Science ®Google Scholar
• Guranda , D.T. ; van Langen , L.M. ; van Rantwijk , F. ; Sheldon , R.A. ; Švedas , V.K. Highly Efficient and Enantioselective Enzymatic Acylation of Amines in Aqueous Medium . Tetrahedron: Asymmetry 2001 , 12 , 1645 – 1650 .
   Web of Science ®Google Scholar
• Li , D.C. ; Cheng , S.W. ; Wei , D.Z. ; Ren , Y.H. ; Zhang , D.R. Production of Enantiomerically Pure (S)-β-Phenylalanine and (R)-β-Phenylalanine by Penicillin G Acylase From Escherichia coli in Aqueous Medium . Biotechnol. Lett. 2007 , 29 , 1825 – 1830 .
   PubMed Web of Science ®Google Scholar
• Zhiryakova , D. ; Guncheva , M. ; Ivanov , I. ; Stambolieva , N. Hydrolysis of Phenylacetanilides Catalyzed by Penicillin G Acylase From Alcaligenes faecalis: Sensitivity of the Reaction to Substitution in the Leaving Group . Catal. Commun. 2009 , 11 , 196 – 201 .
   Web of Science ®Google Scholar
• Gong , X.Y. ; Su , E.Z. ; Wang , P.X. ; Wei , D.Z. Alcaligenes faecalis Penicillin G Acylase-Catalyzed Enantioselective Acylation of D,L-Phenylalanine and Derivatives in Aqueous Medium . Tetrahedron Lett. 2011 , 52 , 5398 – 5402 .
   Web of Science ®Google Scholar
• Cheng , S.W. ; Song , Q.X. ; Wei , D.Z. ; Gao , B.X. High-Level Production Penicillin G Acylase From Alcaligenes faecalis in Recombinant Escherichia coli With Optimization of Carbon Sources . Enzyme Microbial Technol. 2007 , 41 , 326 – 330 .
   Web of Science ®Google Scholar
• Tan , C.Y.K. ; Weavera , D.F. A One-Pot Synthesis of 3-Amino-3-aryl-propionic Acids . Tetrahedron 2002 , 58 , 7449 – 7461 .
   Web of Science ®Google Scholar
• Shewale , J.G. ; Kumar , K.K. ; Ambekar , G.R. Evaluation of Determination of 6-Aminopenicillanic Acid by p-Dimethylminobenzaldehyde . Biotechnol. Technol. 1987 , 1 , 69 – 72 .
   Google Scholar