Synthesis of glycosyl amino acids by light-induced coupling of photoreactive amino acids with glycosylamines and 1-C-aminomethyl glycosides

Carbohydrate Research

Volumn 340, Issue 4, 2005, Pages 557-566

  Simo, Ondrej ^b   Lee, Vincent P ^a   Davis, Alexander S ^a   Kreutz, Christian ^a   Gross, Paul H ^b   Jones, Patrick R ^b   Michael, Katja ^a  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

C Glycosides; Glycosyl amino acids; Photochemical reaction; Transamidation

Indexed keywords

AMINES; IRRADIATION; PHOTOCHEMICAL REACTIONS; PHOTOREACTIVITY; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

GLYCOSYL AMINO ACIDS; LIGHT-INDUCED COUPLING; PHOTOREACTIVE ASPARTATES;

AMINO ACIDS;

ACETIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; AMINOGLYCOSIDE DERIVATIVE; AMINOSUGAR; ASPARAGINE DERIVATIVE; ASPARTIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; GLUTAMINE DERIVATIVE; GLYCOSIDE; INDOLE DERIVATIVE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; LIGHT; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET IRRADIATION;

ACYLATION; AMINO ACIDS; ASPARAGINE; ASPARTIC ACID; CARBOHYDRATE CONFORMATION; DISACCHARIDES; GLUCOSIDES; GLYCOCONJUGATES; GLYCOSIDES; GLYCOSYLATION; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ULTRAVIOLET RAYS;

EID: 13844321256     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.12.023     Document Type: Article

References (33)

1. M. Bodanszky, and S. Natarajan J. Org. Chem. 40 1975 2495 2499
2. M. Bodanszky, and J.Z. Kwei Int. J. Pept. Protein Res. 12 1978 69 74
3. J.P. Tam, M.W. Riemen, and R.B. Merrifield Pept. Res. 1 1988 6 18
4. B. Amit, D.A. Ben-Efraim, and A. Patchornik J. Am. Chem. Soc. 98 1976 843 844
5. G. Goissis, B.W. Erickson, and R.B. Merrifield Pept., Proc. Am. Pept. Symp., 5th 1977 559 561
6. S. Pass, B. Amit, and A. Patchornik J. Am. Chem. Soc. 103 1981 7674 7675
7. K.C. Nicolaou, B.S. Safina, and N. Winssinger Synlett SI 2001 900 903
8. C. Helgen, and C.G. Bochet Synlett 2001 1968 1970
9. C. Helgen, and C.G. Bochet J. Org. Chem. 68 2003 2483 2486
10. K. Vizvardi, C. Kreutz, A.S. Davis, V.P. Lee, B.J. Philmus, O. Simo, and K. Michael Chem. Lett. 32 2003 348 349
11. G. Papageorgiou, D.C. Ogden, A. Barth, and E.E.T. Corrie J. Am. Chem. Soc. 121 1999 6503 6504
12. G. Papageorgiou, and J.E.T. Corrie Tetrahedron 56 2000 8197 8205
13. J. Morrison, P. Wan, J.E.T. Corrie, and G. Papageorgiou Photochem. Photobiol. Sci. 1 2002 960 969
14. G. Papageorgiou, M. Lukeman, P. Wan, and J.E.T. Corrie Photochem. Photobiol. Sci. 3 2004 366 373
15. D.E. Levy, and C. Tang The Chemistry of C-Glycosides 1st ed. 1995 Pergamon Oxford
16. P. Meo, and H.M.I. Osborn The Synthesis of C-Linked Glycosides H.M.I. Osborn Carbohydrates 2003 Elsevier Science Oxford 337 384
17. Z. Györgydeák, and I.F. Pelyvás Glycoscience 1 2001 691 747
18. P.H. Gross, A.H. Franz, and V.V. Samoshin Recent Res. Dev. Org. Chem. 8 2004 255 280
19. P.H. Gross Carbohydr. Polym. 37 1998 215 217
20. P.H. Gross, V.V. Samoshin, A. Franz, J. Gallagher, D. Gremyachinskij, J. Lu, P. Phiasivongsa, O. Simo, and Y.Q. Wei Glycobiology 11 2001 907 908
21. L.-X. Wang, M. Tang, T. Suzuki, K. Kitajima, Y. Inoue, S. Inoue, J.-Q. Fan, and Y.C. Lee J. Am. Chem. Soc. 119 1997 11137 11146
22. C.H. Bolton, L. Hough, and M.Y. Khan Biochem. J. 101 1966 184 190
23. L. Szilágyi, and Z. Györgydeák Carbohydr. Res. 143 1985 21 41
24. H. Waldmann, and H. Kunz Liebigs Ann. Chem. 1983 1712 1725
25. M. Spinola, and R.W. Jeanloz J. Biol. Chem. 245 1970 4158 4162
26. H. Kunz, and H. Waldmann Angew. Chem., Int. Ed. Engl. 24 1985 883 885
27. H. Kunz, H. Waldmann, and J. März Liebigs Ann. Chem. 1989 45 49
28. M. Wagner, S. Dziadek, and H. Kunz Chem. Eur. J. 9 2003 6018 6030
29. K.N. Drew, and P.H. Gross Tetrahedron 47 1991 6113 6126
30. X. Wang, and P.H. Gross J. Org. Chem. 60 1995 1201 1206
31. I. Christiansen-Brams, M. Meldal, and K. Bock J. Chem. Soc., Perkin Trans. 1 1993 1461 1471
32. P. Phiasivongso, J. Gallagher, C.-N. Chen, P.R. Jones, V.V. Samoshin, and P.H. Gross Org. Lett. 4 2002 4587 4590
33. M. Bergmann, L. Zervas, and L. Salzmann Ber. Dtsch. Chem. Ges. 66 1933 1288 1290