Synthesis of 2-C-branched oligo(glyco-amino acid)s (OGAAs) by ring opening of 1,2-cvclopropanecarboxylated sugar donors

Chemistry - A European Journal

Volumn 15, Issue 31, 2009, Pages 7526-7529

  Sridhar, Perali Ramu ^a   Kumar, Patteti Venu ^a   Seshadri, Kalapati ^a   Satyavathi, Rayala ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Carbohydrates; Donor acceptor systems; Glycoamino acids; Glycosylation; Oligosaccharides

Indexed keywords

BOND ACCEPTORS; D-GALACTOSE; DONOR-ACCEPTOR SYSTEMS; ELECTROPHILE; GLYCOAMINO ACIDS; GLYCOSYL; GLYCOSYL DONORS; GLYCOSYLATION REACTIONS; RING OPENING; STEREOSPECIFIC; TRIFLATE;

ACETONITRILE; AMINES; AMINO ACIDS; CARBOHYDRATES; ESTERIFICATION; IODINE; NEGATIVE IONS; OLIGOSACCHARIDES; ORGANIC ACIDS; SUGAR (SUCROSE);

GLYCOSYLATION;

AMINO ACID; CYCLOPROPANE DERIVATIVE; OLIGOSACCHARIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; GLYCOSYLATION; SYNTHESIS;

AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOPROPANES; GLYCOSYLATION; MOLECULAR STRUCTURE; OLIGOSACCHARIDES;

EID: 67949097233     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901022     Document Type: Article

References (36)

1. For recent reviews, see: a) F. Schweizer, Angew. Chem. 2002. 114, 240:
2. Angew. Chem. Int. Ed. 2002, 41, 230;
3. b) S. A. W. Grüner. E. Locardi. E. Lohof, H. Kessler, Chem. Rev. 2002, 102, 491:
4. c) A. Dondoni, A. Marra. Chem. Rev. 2000, 100, 4395.
5. For a compendium of sugar-amino acids, see: M.D.P. Risseeuw, M. Overhand, G.W.J. Fleet, M. I. Simone, Tetrahedron: Asymmetry 2007, 18, 2001.
6. A glyco-amino acid (GAA) is a saccharide attached to a single amino acid by any kind of covalent bond, see: J. P. McDevitt. P.T. Lansbury, Jr., J. Am. Chem. Soc. 1996, 118, 3818.
7. a) A. Rosenthal, K. Shudo. J. Org. Chem. 1972, 37, 4391;
8. b) T. Goto, Y. Toya, T. Ohgi. T. Kondo. Tetrahedron Lett. 1982, 23, 1271 ;
9. c) S. Haranda, T. Kishi, J. Antibiot. 1977, 30, 11:
10. d) P. Garner. J. M. Park, J. Org. Chem. 1990, 55, 3772.
11. H. Seto, M. Koyama. H. Ogino. T. Tsuruoka, Tetrahedron Lett. 1983, 24, 1805.
12. C. S. Stauffer, P. Bhaket, A. W. Fothergill. M. G. Rinaldi, A. Datta, J. Org. Chem. 2007, 72, 9991.
13. G. Casiraghi. L. Colombo, G. Rassu, P. Spanu, J. Org. Chem. 1991, 56. 6523.
14. a) O. Jiménez, G. de La Rosa, R. Lavilla, Angew. Chem. 2005, 117, 6679;
15. Angew. Chem. Int. Ed. 2005, 44, 6521;
16. b) P. R. Sridhar, K. C. Ashalu, S. Chandrasekaran, Org. Lett. 2004, 6, 1777.
17. H. C. Hang, C. R. Bertozzi, J. Am. Chem. Soc. 2001, 123, 1242.
18. a) J. E. Jackman, C. A. Fierke. L. N. Tumey. M. Pirrung, T. Uchiyama, S. H. Tahir, O. Hindsgaul, C. R. H. Raetz. J. Biol. Chem. 2000, 275. 11002:
19. b) X. Li, T. Uchiyama. C. R. H. Raetz, O. Hindsgaul, Org. Lett. 2003, 5, 539.
20. For a recent review on sugar-derived substrates, see: a) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321;
21. for leading reviews, see: b) H. U. Reissig, R. Zimmer. Chem. Rev. 2003, 103, 1151;
22. c) H. U. Reissig. Top. Curr. Chem. 1988, 144, 73:
23. d) E. Wenkert. Acc. Chem. Res. 1980, 13, 27.
24. a) J. Beyer, R. Madsen. J. Am. Chem. Soc. 1998, 120, 12137;
25. b) J. Beyer. P. R. Skaanderup. R. Madsen, J. Am. Chem. Soc. 2000, 122, 9575.
26. a) T. Linker. K. Hartmann, T. Sommermann, D. Scheutzow, E. Ruckdeschel. Angew. Chem. 1996, 108, 1819;
27. Angew. Chem. Int. Ed. Engl. 1996, 35, 1730:
28. b) T. Linker. T. Sommermann, F. Kahlenberg. J. Am. Chem. Soc. 1997, 119, 9377.
29. J. Yin. T. Linker. Chem. Eur. J. 2009, 15, 49.
30. a) M. Yu, B. L. Pagenkopf. J. Am. Chem. Soc. 2003, 1275, 8122:
31. b) M. Yu. B. L. Pagenkopf, Org. Lett. 2003. 5. 5099.
32. a) C. V. Ramana. R. Murali, M. Nagarajan, J. Org. Chem. 1997, 62, 7694, and references therein:
33. b) C. Kim, T. Brady, S. H. Kim. E. A. Theodarakis. Synth. Commun. 2004, 34, 1951.
34. TMSOTf has been used as an activator in various reactions of donor-acceptor cyclopropanes.
35. 11C NMR spectra.
36. The site of reactivity was found by acetylating the free hydroxyl group in disaccharide 24 and observing a downfield shift in the signal of the C2 proton in compound 25. Please see the Supporting Information.