Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(6): 888-890
DOI: 10.1055/s-0028-1083372
DOI: 10.1055/s-0028-1083372
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Glycoaminoxy Acids as Novel Sugar Building Blocks
Further Information
Received
13 November 2008
Publication Date:
11 February 2009 (online)
Publication History
Publication Date:
11 February 2009 (online)
Abstract
Glycoaminoxy acids, a new class of sugar building blocks bearing both aminoxy and carboxylic acid functional groups on the sugar ring, have been efficiently synthesized from α-C-allyl glycosides. These compounds can be easily used for the synthesis of an N-oxy-amide-linked disaccharide and glycosyl amino acid mimetics.
Key words
glycoaminoxy acids - glycopeptides - glycomimetics - glycosides - oligosaccharides
- For reviews of sugar amino acids, see:
-
1a
Schweizer F. Angew. Chem. Int. Ed. 2002, 41: 231 -
1b
Gervay-Hague J.Weathers TM. J. Carbohydr. Chem. 2002, 7-9: 867 -
1c
Gruner SAW.Locardi E.Lohof E.Kessler H. Chem. Rev. 2002, 102: 491 -
1d
Chakraborty TK.Ghosh S.Jayaprakash S. Curr. Med. Chem. 2002, 9: 421 -
1e
Chakraborty TK.Srinivasu P.Tapadar S.Mohan BK. J. Chem. Sci. 2004, 116: 187 -
2a
Yang D.Ng F.-F.Li Z.-J.Wu Y.-D.Chan KWK.Wang D.-P. J. Am. Chem. Soc. 1996, 118: 9794 -
2b
Yang D.Qu J.Li B.Ng F.-F.Wang X.-C.Cheung K.-K.Wang D.-P.Wu Y.-D. J. Am. Chem. Soc. 1999, 121: 589 -
2c
Shin I.Lee M.Lee J.Jung M.Lee W.Yoon J. J. Org. Chem. 2000, 65: 7667 -
2d
Yang D.Li B.Ng F.-F.Yan Y.-L.Qu J.Wu Y.-D. J. Org. Chem. 2001, 66: 7303 -
2e
Chen F.Song K.-S.Wu Y.-D.Yang D. J. Am. Chem. Soc. 2008, 130: 743 -
2f
Li X.Wu Y.-D.Yang D. Acc. Chem. Res. 2008, 41: 1428 -
3a
Li X.Yang D. Chem. Commun. 2006, 3367 -
3b
Yang D.Zhang D.-W.Hao Y.Wu Y.-D.Luo S.-W.Zhu N.-Y. Angew. Chem. Int. Ed. 2004, 43: 6719 - 4
Lee M.Lee J.Baek B.Shin I. Synlett 2003, 325 -
5a
Shin I.Lee J. Synlett 2000, 1297 -
5b
Lee M.Lee J.Shin I. Synlett 2002, 1463 -
6a
Peri F.Cipolla L.Rescigno M.La Ferla B.Nicotra F. Bioconjugate Chem. 2001, 12: 325 -
6b
Cipolla L.Rescigno M.Leone A.Peri F.La Ferla B.Nicotra F. Bioorg. Med. Chem. 2002, 10: 1639 - 7
Niikura K.Kamitani R.Kurogochi M.Uematsu R.Shinohara Y.Nakagawa H.Deguchi K.Monde K.Kondo H.Nishimura S.-I. Chem. Eur. J. 2005, 11: 3825 - 8
Shao J.Tam JP. J. Am. Chem. Soc. 1995, 117: 3893 - 9
Esser-Kahn AP.Francis MB. Angew. Chem. Int. Ed. 2008, 47: 3751 - 10
Knör S.Modlinger A.Poethko T.Schottelius M.Wester H.-J.Kessler H. Chem. Eur. J. 2007, 13: 6082 -
11a
Liu F.Stephen AG.Fisher RJ.Burke TR. Bioorg. Med. Chem. Lett. 2008, 18: 1096 -
11b
Liu F.Stephen AG.Waheed AA.Aman MJ.Freed EO.Fisher RJ.Burke TR. ChemBioChem 2008, 9: 2000 -
12a
Rodriguez EC.Marcaurelle LA.Bertozzi CR. J. Org. Chem. 1998, 63: 7134 -
12b
Duléry V.Renaudet O.Philouze C.Dumy P. Carbohydr. Res. 2007, 342: 894 -
13a
Brask J.Jensen KJ. J. Pept. Sci. 2000, 6: 290 -
13b
Brask J.Jensen KJ. Bioorg. Med. Chem. Lett. 2001, 11: 697 -
13c
Tofteng AP.Hansen TH.Brask J.Nielsen J.Thulstrup PW.Jensen KJ. Org. Biomol. Chem. 2007, 5: 2225 -
13d
Jiménez-Castells C.de la Torre BG.Gutiérrez Gallego R.Andreu D. Bioorg. Med. Chem. Lett. 2007, 17: 5155 -
14a
Xie J. Eur. J. Org. Chem. 2002, 3411 -
14b
Xie J. Carbohydr. Res. 2003, 338: 399 -
14c
Durrat F.Xie J.Valéry JM. Tetrahedron Lett. 2004, 45: 1477 -
14d
Ménand M.Blais J.-C.Hamon L.Valéry J.-M.Xie J. J. Org. Chem. 2005, 70: 4423 -
14e
Ménand M.Blais J.-C.Valéry J.-M.Xie J. J. Org. Chem. 2006, 71: 3295