A modified synthesis and serological evaluation of neoglycoproteins containing the natural disaccharide of PGL-I from Mycobacterium leprae

Bioorg Med Chem Lett. 2010 Jun 1;20(11):3250-3. doi: 10.1016/j.bmcl.2010.04.072. Epub 2010 Apr 21.


In order to generate substantial amounts of neoglycoconjugate needed for commercialization of diagnostic kits and high-throughput detection of leprosy, we developed a facile and high-yield synthesis of the corresponding disaccharide. Herein, the non-reducing disaccharide segment of phenolic glycolipid I from Mycobacterium leprae, O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1-->4)-O-2,3-di-O-methyl-alpha-L-rhamnopyranose was synthesized by an improved procedure. The disaccharide was efficiently conjugated to bovine/human serum albumin, via acyl-azide intermediate, to form natural disaccharide-BSA/HSA neoglycoproteins that showed a high activity in serodiagnosis of leprosy. The disaccharide incorporated into the proteins was accurately measured by MALDI-TOF mass spectrometry. The serological activities of the neoglycoproteins against pooled human lepromatous leprosy sera were measured by ELISA and they were detectable at picogram amounts.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antigens, Bacterial / chemistry*
  • Carbohydrate Sequence
  • Disaccharides / chemistry*
  • Enzyme-Linked Immunosorbent Assay
  • Glycolipids / chemistry*
  • Glycoproteins / blood
  • Glycoproteins / chemical synthesis*
  • Glycoproteins / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization


  • Antigens, Bacterial
  • Disaccharides
  • Glycolipids
  • Glycoproteins
  • phenolic glycolipid I, Mycobacterium leprae