Alcalase‐Catalyzed, Kinetically Controlled Synthesis of a Precursor Dipeptide of RGDS in Organic Solvents

References

• Pierschbacher , M. D. and Ruoslahti , E. 1984 . Variants of the cell recognition site of fibronectin that retain attachment‐promoting activity . Proc. Natl. Acad. Sci. USA , 81 : 5985 – 5988 .
   PubMed Web of Science ®Google Scholar
• Yamamoto , Y. , Tsutsumi , Y. and Mayumi , T. 2002 . Molecular design of bioconjugated cell adhesion peptide with a water‐soluble polymeric modifier for enhancement of antimetastatic effect . Curr. Drug Targets , 3 : 123 – 130 .
   PubMed Web of Science ®Google Scholar
• Duong , L. T. , Lakkakorpi , P. , Nakamura , I. and Rodan , G. A. 2000 . Integrins and signaling in osteoclast function . Matrix Biol. , 19 : 97 – 105 .
   PubMed Web of Science ®Google Scholar
• Coller , B. S. 2001 . Anti‐GPIIb/IIIa drugs: current strategies and future directions. Thromb . Haemost. , 86 : 427 – 443 .
   Google Scholar
• Hallahan , D. E. , Qu , S. , Geng , L. , Cmelak , A. , Chakravarthy , A. , Martin , W. , Scarfone , C. and Giorgio , T. 2001 . Radiation‐mediated control of drug delivery . Am. J. Clin. Oncol. , 24 : 473 – 478 .
   PubMed Web of Science ®Google Scholar
• Aguzzi , M. S. , Facchiano , F. , Ribatti , D. , Gaeta , R. , Casadio , R. , Rossi , I. , Capogrossi , M. C. and Facchiano , A. 2004 . A novel RGDS‐analog inhibits angiogenesis in vitro and in vivo . Biochem. Biophys. Res. Comm. , 321 : 809 – 814 .
   PubMedGoogle Scholar
• Aguzzi , M. S. , Giampietri , C. , De Marchis , F. , Padula , F. , Gaeta , R. , Ragone , G. , Capogrossi , M. C. and Facchiano , A. 2004 . RGDS peptide induces caspase 8 and caspase 9 activation in human endothelial cells . Blood , 103 : 4180 – 4187 .
   PubMed Web of Science ®Google Scholar
• Buckley , C. D. , Pilling , D. , Henriquez , N. V. , Parsonage , G. , Threlfall , K. , Scheel‐Toellner , D. , Simmons , D. L. , Akbar , A. N. , Lord , J. M. and Salmon , M. 1999 . RGD peptides induce apoptosis by direct caspase‐3 activation . Nature , 397 : 534 – 539 .
   PubMed Web of Science ®Google Scholar
• Adderley , S. R. and Fitzgerard , D. J. 2000 . Glycoprotein IIb/IIIa antagonists induce apoptosis in rat cardiomyocytes by caspase‐3 activation . J. Biol. Chem. , 275 : 5760 – 5766 .
   PubMedGoogle Scholar
• Castel , S. , Pagan , R. , Mitjans , F. , Piulats , J. , Goodman , S. , Jonczyk , A. , Huber , F. , Vilaro , S. and Reina , M. 2001 . RGD peptides and monoclonal antibodies, antagonists of alpha(v)‐integrin, enter the cells by independent endocytic pathways . Lab. Invest. , 81 : 1615 – 1626 .
   PubMed Web of Science ®Google Scholar
• Gill , I. , López‐Fandiño , R. , Jorba , X. and Vulfson , E. N. 1996 . Biologically active peptides and enzymatic approaches to their production . Enzyme Microb. Technol. , 18 : 162 – 183 .
   Web of Science ®Google Scholar
• Kimura , Y. , MurayaAraki , Y. , Matsuoka , H. , Nakanishi , K. and Matsuno , R. 1990 . Synthesis of peptides consisting of essential amino acids by a reactor system using three proteinases and an organic solvent . Agric. Biol. Chem. , 54 : 3331 – 3333 .
   PubMed Web of Science ®Google Scholar
• Fernandez , M. M. , Margot , A. O. , Falender , C. A. , Blanch , H. W. and Clark , D. S. 1995 . Enzymatic synthesis of peptides containing unnatural amino acids . Enzyme Microb. Technol. , 17 : 964 – 971 .
   PubMed Web of Science ®Google Scholar
• Krix , G. , Eichhorn , U. , Jakubke , H. D. and Kula , M. R. 1997 . Protease‐catalyzed synthesis of new hydrophobic dipeptides containing non‐proteinogenic amino acids . Enzyme Microb. Technol. , 21 : 252 – 257 .
   Web of Science ®Google Scholar
• Clapés , P. , Adlercreutz , P. and Mattiasson , B. 1990 . Enzymatic peptide synthesis in organic media: nucleopile specificity and medium engineering in α‐chymotrypsin‐catalyzed reactions . Appl. Biochem. Biotechnol. , 12 : 376 – 386 .
   Google Scholar
• Zhang , X. Z. , Wang , X. , Chen , S. M. , Fu , X. O. , Wu , X. X. and Li , C. H. 1996 . Protease‐catalyzed small peptide synthesis in organic media . Enzyme Microb. Technol. , 19 : 538 – 544 .
   Web of Science ®Google Scholar
• So , J. E. , Shik , J. S. and Kim , B. G. 2000 . Protease‐catalyzed tripeptide (RGD) synthesis . Enzyme Microb. Technol. , 26 : 108 – 114 .
   PubMed Web of Science ®Google Scholar
• Zhang , L. Q. , Xu , L. , Yang , X. C. , Wu , X. X. and Zhang , X.‐Z. 2003 . Lipase‐catalyzed synthesis of precursor dipeptide of RGD in aqueous water‐miscible organic solvents . Prep. Biochem. Biotechnol. , 33 : 1 – 12 .
   PubMed Web of Science ®Google Scholar
• Chen , S. T. , Chen , S. Y. and Wang , K. T. 1992 . Kinetically controlled peptide bond formation in anhydrous alcohol catalyzed by the industrial protease alcalase . J. Org. Chem. , 57 : 6960 – 6965 .
   Web of Science ®Google Scholar
• Klein , J. U. , Prykhodzka , A. and Čeřovský , V. 2000 . The Applicability of subtilisin Carlsberg in peptide synthesis . J. Peptide Sci. , 6 : 541 – 549 .
   PubMed Web of Science ®Google Scholar
• Klibanov , A. M. 2001 . Improving enzymes by using them in organic solvents . Nature , 409 : 241 – 246 .
   PubMed Web of Science ®Google Scholar
• Laane , C. , Boeren , S. , Vos , K. and Veeger , C. 1987 . Rules for optimization of biocatalysis in organic solvents . Biotechnol. Bioeng. , 30 : 81 – 87 .
   PubMed Web of Science ®Google Scholar
• Okazaki , S. Y. , Goto , M. and Furusaki , S. 2000 . Surfactant‐protease complex as a novel biocatalyst for peptide synthesis in hydrophilic organic solvents . Enzyme Microb. Technol. , 26 : 159 – 164 .
   PubMed Web of Science ®Google Scholar
• Klibanov , A. M. 1986 . Enzymes that work in organic solvents . Chem. Tech. , : 355 – 359 .
   Google Scholar
• Lozano , P. , Cano , J. , Iborra , J. L. and Manjón , A. 1993 . Glycylglycylphenylalaninamide synthesis catalysed by papain in a medium containing polyols . Biotechnol. Appl. Biochem. , 18 : 67 – 74 .
   PubMed Web of Science ®Google Scholar
• Isono , Y. and Nakajima , M. 2000 . Enzymic peptide synthesis using a microaqueous highly concentrated amino acid mixture . Proc. Biochem. , 36 : 275 – 278 .
   Web of Science ®Google Scholar
• Erbeldinger , M. , Ni , X. and Halling , P. J. 1998 . Enzymatic synthesis with mainly undissolved substrates at very high concentrations . Enzyme Microb. Technol. , 23 : 141 – 148 .
   Web of Science ®Google Scholar