Synthesis of an N-linked glycopeptide from vitamin K-dependent protein S

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11995-12006

  Holm, Björn ^a   Linse, Sara ^b   Kihlberg, Jan ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Glycopeptides; Protecting groups; Protein S; Solid phase synthesis

Indexed keywords

GLYCOPEPTIDE; PROTEIN S; VITAMIN K GROUP;

ANTICOAGULATION; ARTICLE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DEACETYLATION; DIMERIZATION; DRUG SYNTHESIS; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID PHASE EXTRACTION;

EID: 0032564016     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83053-6     Document Type: Article

References (28)

1. Dahlbäck B. Biochem. J. 1983;209:847-856.
2. Linse S, Härdig Y, Schultz DA, Dahlbäck B. J. Biol. Chem. 1997;272:14658-14665.
3. O'Connor S, Imperiali B. Chemistry & Biology 1996;3:803-812.
4. Montreuil J. Adv. Carbohyhdr. Chem. Biochem. 1980;37:157-223.
5. Cohen-Anisfeld ST, Lansbury Jr PT. J. Am. Chem. Soc. 1993;115:10531-10537.
6. Vetter D, Tumelty D, Singh SK, Gallop MA. Angew. Chem. Int. Ed. Engl. 1995;34:60-62.
7. Offer J, Quibell M, Johnson T. J. Chem. Soc., Perkin Trans. 1 1996:175-182.
8. Meldal M. Glycopeptide synthesis. In: Lee YC, Lee RT, eds. Neoglycoconjugates: Preparation and applications. San Diego: Academic Press, Inc., 1994:145-198.
9. Garg HG, von dem Bruch K, Kunz H. Adv. Carbohydr. Chem. Biochem. 1994;50:277-310.
10. Paul B, Korytnyk W. Carbohydr. Res. 1978;67:457-468.
11. Spetzler JC, Meldal M, Meinjohanns E, Steinaa L, Mouritsen S, Bock K. J. Peptide Sci. 1997;3:397-414.
12. Kunz H, Waldman H, März J. Liebigs Ann. Chem. 1989:45-49.
13. Elofsson M, Salvador LA, Kihlberg J. Tetrahedron 1997;53:369-390.
14. Broddefalk J, Bergquist K-E, Kihlberg J. Tetrahedron Lett. 1996;37:3011-3014.
15. Broddefalk J, Bäcklund J, Almqvist F, Johansson M, Holmdahl R, Kihlberg J. J. Am. Chem. Soc.;submitted.
16. Broddefalk J, Bergquist K-E, Kihlberg J. Tetrahedron 1998;54:12047-12070.
17. Meinjohanns E, Meldal M, Paulsen H, Dwek RA, Bock K. J. Chem. Soc., Perkin Trans. 1 1998:549-560.
18. Inazu T, Kobayashi K. Synlett 1993:869-870.
19. Maunier V, Boullanger P, Lafont D. J. Carbohydr. Chem. 1997;16:231-235.
20. Cameron LR, Holder JL, Meldal M, Sheppard RC. J. Chem. Soc. Perkin Trans. 1 1988:2895-2901.
21. Rink H. Tetrahedron Lett. 1987;28:3787-3790.
22. Bernatowicz MS, Daniels SB, Köster H. Tetrahedron Lett. 1989;30:4645-4648.
23. König W, Geiger R. Chem. Ber. 1970;103:788-798.
24. Carpino LA. J. Am. Chem. Soc. 1993;115:4397-4398.
25. Flegel M, Sheppard RC. J. Chem. Soc., Chem. Commun. 1990:536-538.
26. Dryland A, Sheppard RC. J. Chem. Soc. Perkin Trans. 1 1986:125-137.
27. Urge L, Otvos Jr. L, Lang E, Wroblewski K, Laczko I, Hollosi M. Carbohydr. Res. 1992;235:83-93.
28. Urge L, Jackson DC, Gorbics L, Wroblewski K, Graczyk G, Otvos Jr. L. Tetrahedron 1994;50:2373-2390.