title: Chemical diversification of sialic acid glycosides by stereospecific, chemoselective deamination.
abstract: Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late-stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202 (USA).
authors.forename: Chandrasekhar
authors.initials: C
authors.lastname: Navuluri
authors.forename: David
authors.initials: D
authors.lastname: Crich
mesh_terms: D003641:Deamination; D006027:Glycosides / Q000737:chemistry*; D015538:Nitrosation; D012794:Sialic Acids / Q000737:chemistry*
chemical_list: D006027:Glycosides; D012794:Sialic Acids
keywords: deamination; diversification; glycosylation; nitrosation; sialic acids
references.citation: Carbohydr Res. 2008 Jul 21;343(10-11):1540-52
references.pmid: 18452900
references.citation: J Org Chem. 2007 Sep 28;72(20):7794-7
references.pmid: 17824651
references.citation: J Am Chem Soc. 2009 Mar 11;131(9):3138-9
references.pmid: 19215076
references.citation: Angew Chem Int Ed Engl. 2012 Oct 29;51(44):11014-8
references.pmid: 23038623
references.citation: J Am Chem Soc. 2006 Jun 7;128(22):7124-5
references.pmid: 16734441
references.citation: Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3049-52
references.pmid: 20333634
references.citation: J Org Chem. 2007 Mar 30;72(7):2387-91
references.pmid: 17338570
references.citation: J Org Chem. 2009 Jun 5;74(11):4383-6
references.pmid: 19413275
references.citation: Chemistry. 2010 Feb 8;16(6):1754-60
references.pmid: 20066711
references.citation: Angew Chem Int Ed Engl. 2008;47(47):8995-7
references.pmid: 18846513
references.citation: J Org Chem. 2011 May 20;76(10):3691-709
references.pmid: 21428425
references.citation: Bioconjug Chem. 2006 Nov-Dec;17(6):1537-44
references.pmid: 17105234
references.citation: ACS Chem Biol. 2012 Jul 20;7(7):1232-40
references.pmid: 22583967
references.citation: Angew Chem Int Ed Engl. 2011 Sep 26;50(40):9391-5
references.pmid: 21948436
references.citation: J Biol Chem. 2011 Sep 9;286(36):31610-22
references.pmid: 21757734