Download PDF
Synthesis 2002(6): 0726-0732
DOI: 10.1055/s-2002-25762
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Precursor of Bioactive Pentapeptide OGP-(10-14) and the Fragment of Enkephalin Catalyzed by MCM-22 Immobilized or Free Proteases in Organic Solvents

Ping Liua, Yun-hua Ye*a, Gui-ling Tiana, Kin-Sing Leeb, Man-Sau Wongb, Wai-hung Lob
a The Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, Department of Chemistry, Peking University, Beijing, 100871, PRC
b Open Laboratory of Chirotechnology and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, PRC
Fax: +86(10)62751708; e-Mail: yhye@pku.edu.cn;
Further Information

Publication History

Received 16 January 2002
Publication Date:
26 April 2002 (online)

    Permissions and Reprints All articles of this category

Abstract

Full enzymatic synthesis of a precursor of osteogenic growth peptide fragment (10-14), Z-Tyr-Gly-Phe-Gly-Gly-OEt, was accomplished using immobilized proteases on molecular sieve MCM-22 by adsorption as catalyst via 3+2 synthetic route for the first time. The reuse time of immobilized enzyme was dependent on concrete reaction system. Compared with free enzyme, the reaction rate catalyzed by immobilized enzyme was remarkably enhanced and its synthetic yield was also increased in most cases. The effects of water content and the added amount of Et3N on synthesis of fragments of bioactive peptides including OGP-(10-14) and enkephalin by immobilized enzymes were different from free enzyme.

Key words

immobilized enzyme - MCM-22 - OGP-(10-14) - enzymatic peptide synthesis - organic solvents

    References

  • 1 Wong CH. Wang KT. Experiantia  1991,  47:  1123 
    Google Scholar
  • 2 Ye Y.-H. Tian G.-L. Xing G.-W. Dai D.-C. Chen G. Li C.-X. Tetrahedron  1998,  54:  12585 
    CrossrefGoogle Scholar
  • 3 Xing G.-W. Tian G.-L. Ye Y.-H. J. Peptide Res.  1998,  52:  300 
    Google Scholar
  • 4 Basso A. Martin LD. Ebert C. Gardossi L. Linda P. Chem. Commun.  2000,  467 
    CrossrefGoogle Scholar
  • 5 Miyazawa T. Nakajo S. Nishikawa M. Hamahara K. Imagawa K. Ensatsu E. Yanagihara R. Yamada T. J. Chem. Soc., Perkin Trans. 1  2001,  82 
    CrossrefGoogle Scholar
  • 6 Okazak S.-y. Goto M. Furusaki S. Enzyme Microb. Technol.  2000,  26:  159 
    CrossrefGoogle Scholar
  • 7 Liu P. Tian GL. Ye YH. Chem. J. Chin. Univ.  2001,  1342 
    Google Scholar
  • 8 Xing GW. Li XW. Tian GL. Ye YH. Tetrahedron  2000,  56:  3517 
    CrossrefGoogle Scholar
  • 9 Liu BH. Hu RQ. Deng JQ. Analyst  1997,  122:  821 
    CrossrefGoogle Scholar
  • 10 Liu BH. Hu RQ. Deng JQ. Anal. Chem.  1997,  69:  2343 
    CrossrefGoogle Scholar
  • 11 Mukherjea RN. Bhattacharya P. Ghosh BK. Taraphadar DK. Biotechnol. Bioengin.  1977,  19:  1259 
    Google Scholar
  • 12 Iyengar L. Prabhakara Rao AVS. J. Gen. Appl. Microbiol.  1981,  27:  339 
    Google Scholar
  • 13 Li XF. He J. Duan X. Zhu YX. Acta Chim. Sinica  2000,  58:  167 ; Chem. Abstr. 2000, 132, 319240z
    Google Scholar
  • 14 Diaz JF. Balkus KJ. J. Mol. Cat. B: Enzymatic  1996,  2:  115 
    Google Scholar
  • 15 Gonçalves APV. Lopes JM. Lemos F. Ramôa Ribeiru F. Prazeres DMF. Cabral JMS. Aires-Barros MR. J. Mol. Cat. B: Enzymatic  1996,  1:  53 
    Google Scholar
  • 16 Chen YC. Bab I. Mansur N. Muhlrad A. Shteyer A. Namdar-Attar M. Gavish H. Vidson M. Chorev M. J. Peptide Res.  2000,  56:  147 
    Google Scholar
  • 17 Bab I. Gazit D. Chorev M. Muhlrad A. Shteyer A. Greenberg Z. Namdar M. Kahn A. EMBO J.  1992,  11:  1867 
    Google Scholar
  • 18 Bab I. Smith E. Gavish H. Attar-Namdar M. Chorev M. Chen YC. Muhlrad A. Birnbaum MJ. Gary S. Frenkel B. J. Biol. Chem.  1999,  274:  14474 
    CrossrefGoogle Scholar
  • 19 Greenberg Z. Chorev M. Muhlrad A. Shteyer A. Namdar M. Mausm N. Bab I. Biochim. Biophys. Acta.  1993,  1178:  273 
    Google Scholar
  • 20 Robinson D. Bab I. Nevo Z. J. Bone Miner. Res.  1995,  10:  690 
    Google Scholar
  • 21 Greenberg Z. Gavish H. Chorev M. Muhlrad A. Shteyer A. Attar-Namdar M. Tartakovsky A. Bab I. J. Cell. Biochem.  1997,  65:  359 
    CrossrefGoogle Scholar
  • 22 Gurevitch O. Slavin S. Muhlrad A. Shteyer A. Gazit D. Chorev M. Vidson M. Namdar-Attar M. Berger E. Bleiberg I. Bab I. Blood  1996,  88:  4719 
    Google Scholar
  • 23 Liu P. Yan A.-x. Ye Y.-h. Huaxue Tongbo (Chemistry)  2001,  777 
    Google Scholar
  • 25 Wartchow CA. Wang P. Bednarski MD. Callstrom MR. J. Org. Chem.  1995,  60:  2216 
    CrossrefGoogle Scholar
  • 26 Cai MS. Peng SQ. Cheng TM. Dai DH. Wang SN. Li JX. Zhang JL. Cong Y. Liang WS. Wang R. Yang SS. Chen SH. Wu XD. Zhang AZ. Sci. Sin., Ser. B  1988,  31:  444 ; Chem. Abstr. 1989, 110, 39355j
    Google Scholar
  • 27 Nomura R. Nakano T. Yamada Y. Matsuda H. J. Org. Chem.  1991,  56:  4076 
    Google Scholar
  • 28 Beacham J. Bentley PH. Kenner GW. Macleod JK. Mendive JJ. Sheppard RC. J. Chem. Soc. C  1967,  2520 
    CrossrefGoogle Scholar
24

The IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), Eur. J. Biochem. 1984, 138, 9.