A synthesis of a glycopeptide analogue of eel calcitonin

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 55-58

  Mizuno, Mamoru ^a   Muramoto, Ikuyo ^a   Kawakami, Toru ^b   Seike, Makoto ^b   Aimoto, Saburo ^b   Haneda, Katsuji ^a   Inazu, Toshiyuki ^a  

^a NOGUCHI INSTITUTE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITONIN DERIVATIVE; ELCATONIN; GLYCOPROTEIN;

ARTICLE; EEL; NONHUMAN; PEPTIDE ANALYSIS; PROTEIN ANALYSIS; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0031983243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10487-7     Document Type: Article

References (22)

1. Blite D.L. Trends Glycosci. Glycotechnol. 5:1993;81.
2. (a) Peters, S.; Lowary, L.T.; Hindsgaul, O.; Meldal, M. and Bock, K. J. Chem. Soc., Perkin Trans. 1, 1995, 3017.
3. (b) Wong, Y.C.W.; Guile, R.G.; Randemacher, T.W. and Dwek, R.A. Glycoconjugate J, 1993, 10, 227.
4. (c) Reimer, K.B.; Meldal, M.; Kusumoto, S.; Fukase, K. and Bock, K. J. Chem. Soc., Perkin Trans. 1, 1993, 925.
5. (d) Brams, I.C.; Meldal, M. and Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461.
6. (e) Meldal, M. and Bock, K. Tetrahedron Lett., 1990, 31, 6987.
7. (f) Jansson, A.M.; Meldal, M. and Bock, K. Tetrahedron Lett., 1990, 31, 6991.
8. Inazu, T.; Mizuno, M.; Maegami, T. and Haneda, K. "Peptide Chemistry 1996," ed by C. Kitada, Protein Research Foundation, Osaka (1997), pp. 41-44.
9. Wang X.-L., Fan J.-Q., Lee Y.C. Tetrahedron Lett. 37:1996;1975.
10. Haneda K., Inazu T., Yamamoto K., Nakahara Y., Kobata A. Carbohydr. Res. 292:1996;61.
11. (a) Hojo, H. and Aimoto, S. Bull. Chem. Soc. Jpn., 1991, 64, 111.
12. (b) Idem, ibid, 1992, 65, 3055.
13. Kawakami T., Kogure S., Aimoto S. Bull. Chem. Soc. Jpn. 61:1996;3331.
14. Inazu, T. and Kobayashi, K. Synlett, 1993, 869.
15. 4-Methylbenzhydrylamine (MBHA) resin from Peptide Institute, Inc. was used.
16. Solid-phase synthesis in this study was performed via Boc-strategy. Amino acids were coupled as N-α- Boc derivatives by the following side chain protections : Benzyl (Bzl) for Glu, Ser, Thr; cyclohexyl (cHex) for Asp; 2-bromobenzyloxcarbonyl (2-Br-Z) for Tyr; 2-chloro-benzyloxcarbonyl (2-Cl-Z) for Lys (Lys was coupled as Fmoc-Lys(Boc)); benzyloxymethyl (Bom) for His; p-toluenesulfonyl (Tos) for Arg; acetamidomethyl (Acm) for Cys.
17. 1 residues.
18. Coupling reactions of each Mpt-MAs were carried out with a three-fold excess of Boc-Asn(GlcNAc)-OH and Boc-Ser(Bzl)-OH, Fmoc-Cys(Acm)-OH.
19. 1.90. Cys was not observed, because S-Acm group is stable under the above conditions.
20. -1.
21. 5.
22. 1.03.