Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens Journal Article

  


Authors: Keding, S. J.; Endo, A.; Danishefsky, S. J.
Article Title: Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens
Abstract: The synthesis of biologically relevant glycosylamino acids using a non-natural amino acid as the glycosyl acceptor is described. The glycosylation reaction of a monosaccharide tri-chloroacetimidate donor with Fmoc-L-hydroxynorleucine benzyl ester provided the α-O-linked product. Conversely, when the glycosylation reaction was carried out with a glycal epoxide donor, the β-O-linked product predominated. We have used these two complementary glycosylation reactions to synthesize five different glycosylamino acids, each containing the Tn, TF, STn, Lewisy or Globo-H tumor-associated carbohydrate antigens. © 2003 Elsevier Ltd. All rights reserved.
Keywords: mass spectrometry; drug synthesis; tumor antigen; glycosylation; thin layer chromatography; lewis acid; carbohydrate antigen; proton nuclear magnetic resonance; carbon nuclear magnetic resonance; glycosylamino acid; epoxide; monosaccharide; carbohydrate-based antitumor vaccines; amino acid derivative; aminoglycoside derivative; priority journal; article; hydroxynorleucine; benzyl derivative
Journal Title: Tetrahedron
Volume: 59
Issue: 35
ISSN: 0040-4020
Publisher: Elsevier Inc.  
Date Published: 2003-08-25
Start Page: 7023
End Page: 7031
Language: English
DOI: 10.1016/s0040-4020(03)00935-9
PROVIDER: scopus
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-0041657398&partnerID=40&md5=c06448b05be0192eb8a5c6709cbdca06
Notes: Export Date: 12 September 2014 -- Source: Scopus
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MSK Authors
  1. Atsushi Endo
    5 Endo
  2. Stacy J Keding
    9 Keding
  3. Samuel J Danishefsky
    539 Danishefsky
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