Literature DB >> 20462755

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

Jian Zhang1, Delphi Chatterjee, Patrick J Brennan, John S Spencer, Avraham Liav.   

Abstract

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. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID: 20462755      PMCID: PMC2917636          DOI: 10.1016/j.bmcl.2010.04.072

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  9 in total

1.  Chemical synthesis of disaccharides of the specific phenolic glycolipid antigens from Mycobacterium leprae and of related sugars.

Authors:  T Fujiwara; S W Hunter; P J Brennan
Journal:  Carbohydr Res       Date:  1986-05-01       Impact factor: 2.104

2.  A facile synthesis of 3,6-di-O-methyl-D-glucose.

Authors:  A Liav; M B Goren
Journal:  Carbohydr Res       Date:  1986-07-01       Impact factor: 2.104

3.  Synthesis and immunoreactivity of neoglycoproteins containing the trisaccharide unit of phenolic glycolipid I of Mycobacterium leprae.

Authors:  D Chatterjee; S N Cho; C Stewart; J T Douglas; T Fujiwara; P J Brennan
Journal:  Carbohydr Res       Date:  1988-12-01       Impact factor: 2.104

4.  Structure and antigenicity of the major specific glycolipid antigen of Mycobacterium leprae.

Authors:  S W Hunter; T Fujiwara; P J Brennan
Journal:  J Biol Chem       Date:  1982-12-25       Impact factor: 5.157

5.  Role of the cell wall phenolic glycolipid-1 in the peripheral nerve predilection of Mycobacterium leprae.

Authors:  V Ng; G Zanazzi; R Timpl; J F Talts; J L Salzer; P J Brennan; A Rambukkana
Journal:  Cell       Date:  2000-10-27       Impact factor: 41.582

6.  Chemical synthesis of the trisaccharide unit of the species-specific phenolic glycolipid from Mycobacterium leprae.

Authors:  T Fujiwara; G O Aspinall; S W Hunter; P J Brennan
Journal:  Carbohydr Res       Date:  1987-06-01       Impact factor: 2.104

7.  Chemical synthesis and seroreactivity of O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----9)-oxynonanoyl-bovine serum albumin--the leprosy-specific, natural disaccharide-octyl-neoglycoprotein.

Authors:  D Chatterjee; S N Cho; P J Brennan; G O Aspinall
Journal:  Carbohydr Res       Date:  1986-11-15       Impact factor: 2.104

8.  Chemical synthesis and serology of disaccharides and trisaccharides of phenolic glycolipid antigens from the leprosy bacillus and preparation of a disaccharide protein conjugate for serodiagnosis of leprosy.

Authors:  T Fujiwara; S W Hunter; S N Cho; G O Aspinall; P J Brennan
Journal:  Infect Immun       Date:  1984-01       Impact factor: 3.441

9.  Role of alpha-dystroglycan as a Schwann cell receptor for Mycobacterium leprae.

Authors:  A Rambukkana; H Yamada; G Zanazzi; T Mathus; J L Salzer; P D Yurchenco; K P Campbell; V A Fischetti
Journal:  Science       Date:  1998-12-11       Impact factor: 47.728

  9 in total
  4 in total

1.  Endemic leprosy in New York City.

Authors:  William R Levis; Lilly-Rose Paraskevas; Mark Jacobson; John Spencer; Trudy Spencer; Frank Martiniuk
Journal:  Arch Dermatol       Date:  2011-05

Review 2.  Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009-2010.

Authors:  David J Harvey
Journal:  Mass Spectrom Rev       Date:  2014-05-26       Impact factor: 10.946

3.  Analysis of antibody responses to Mycobacterium leprae phenolic glycolipid I, lipoarabinomannan, and recombinant proteins to define disease subtype-specific antigenic profiles in leprosy.

Authors:  John S Spencer; Hee Jin Kim; William H Wheat; Delphi Chatterjee; Marivic V Balagon; Roland V Cellona; Esterlina V Tan; Robert Gelber; Paul Saunderson; Malcolm S Duthie; Stephen T Reece; William Burman; Robert Belknap; William R Mac Kenzie; Annemieke Geluk; Linda Oskam; Hazel M Dockrell; Patrick J Brennan
Journal:  Clin Vaccine Immunol       Date:  2010-12-22

4.  Synthetic Phenolic Glycolipids for Application in Diagnostic Tests for Leprosy.

Authors:  J Hessel M van Dijk; Anouk van Hooij; L Melanie Groot; Jolijn Geboers; Rosita Moretti; Els Verhard-Seymonsbergen; Danielle de Jong; Gijs A van der Marel; Paul L A M Corstjens; Jeroen D C Codée; Annemieke Geluk
Journal:  Chembiochem       Date:  2021-02-10       Impact factor: 3.164

  4 in total

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