Chemical synthesis and seroreactivity of a neoantigen containing the oligosaccharide hapten of the Mycobacterium tuberculosis-specific phenolic glycolipid

M. Daffe, Sangnae Cho, D. Chatterjee, P. J. Brennan

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The report of a major triglycosyl phenol phthiocerol (phenolic) glycolipid in some strains of Mycobacterium tuberculosis that resembles the phenolic glycolipid I of Mycobacterium leprae raised the prospects of a specific serodiagnostic tool for human tuberculosis. The terminal diglycosyl unit of the M. tuberculosis product was synthesized and converted to a corresponding neoglycoprotein, the O-(2,3,4-tri-O-methyl-α-L-fucopyranosyl)-(1→3)-O-α-L- rhamnopyranosyl)-(1→9)-oxynonanoyl-bovine serum albumin, and applied, in ELISA, to sera from individuals with tuberculosis. Although the correlation coefficient between the synthetic product and the native glycolipid was excellent, the seroreactivity rate of tuberculous sera was disappointing; only 24 of 119 sera from tuberculosis patients showed evidence of anti-glycolipid antibodies. In isolates of M. tuberculosis from tuberculosis patients the glycolipid was present in only 1 of 11. A partially deglycosylated version was present in two other isolates; however, most isolates lacked the glycolipid. Accordingly, while the results, unlike those of others, do not portend a future for this form of serodiagnosis in the management of tuberculosis, they offer intriguing hints as to the basis of the variable immunogenicity and pathogenicity of strains of M. tuberculosis.

Original languageEnglish
Pages (from-to)161-168
Number of pages8
JournalJournal of Infectious Diseases
Volume163
Issue number1
DOIs
Publication statusPublished - 1991 Jan 1

Fingerprint

Haptens
Glycolipids
Phenol
Oligosaccharides
Mycobacterium tuberculosis
Tuberculosis
Serum
Mycobacterium leprae
Serologic Tests
Bovine Serum Albumin
Virulence
Anti-Idiotypic Antibodies
Glycoproteins
Enzyme-Linked Immunosorbent Assay

All Science Journal Classification (ASJC) codes

  • Immunology and Allergy
  • Infectious Diseases

Cite this

@article{5c3262edcb9349c9a2eb5f6888688fe3,
title = "Chemical synthesis and seroreactivity of a neoantigen containing the oligosaccharide hapten of the Mycobacterium tuberculosis-specific phenolic glycolipid",
abstract = "The report of a major triglycosyl phenol phthiocerol (phenolic) glycolipid in some strains of Mycobacterium tuberculosis that resembles the phenolic glycolipid I of Mycobacterium leprae raised the prospects of a specific serodiagnostic tool for human tuberculosis. The terminal diglycosyl unit of the M. tuberculosis product was synthesized and converted to a corresponding neoglycoprotein, the O-(2,3,4-tri-O-methyl-α-L-fucopyranosyl)-(1→3)-O-α-L- rhamnopyranosyl)-(1→9)-oxynonanoyl-bovine serum albumin, and applied, in ELISA, to sera from individuals with tuberculosis. Although the correlation coefficient between the synthetic product and the native glycolipid was excellent, the seroreactivity rate of tuberculous sera was disappointing; only 24 of 119 sera from tuberculosis patients showed evidence of anti-glycolipid antibodies. In isolates of M. tuberculosis from tuberculosis patients the glycolipid was present in only 1 of 11. A partially deglycosylated version was present in two other isolates; however, most isolates lacked the glycolipid. Accordingly, while the results, unlike those of others, do not portend a future for this form of serodiagnosis in the management of tuberculosis, they offer intriguing hints as to the basis of the variable immunogenicity and pathogenicity of strains of M. tuberculosis.",
author = "M. Daffe and Sangnae Cho and D. Chatterjee and Brennan, {P. J.}",
year = "1991",
month = "1",
day = "1",
doi = "10.1093/infdis/163.1.161",
language = "English",
volume = "163",
pages = "161--168",
journal = "Journal of Infectious Diseases",
issn = "0022-1899",
publisher = "Oxford University Press",
number = "1",

}

Chemical synthesis and seroreactivity of a neoantigen containing the oligosaccharide hapten of the Mycobacterium tuberculosis-specific phenolic glycolipid. / Daffe, M.; Cho, Sangnae; Chatterjee, D.; Brennan, P. J.

In: Journal of Infectious Diseases, Vol. 163, No. 1, 01.01.1991, p. 161-168.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chemical synthesis and seroreactivity of a neoantigen containing the oligosaccharide hapten of the Mycobacterium tuberculosis-specific phenolic glycolipid

AU - Daffe, M.

AU - Cho, Sangnae

AU - Chatterjee, D.

AU - Brennan, P. J.

PY - 1991/1/1

Y1 - 1991/1/1

N2 - The report of a major triglycosyl phenol phthiocerol (phenolic) glycolipid in some strains of Mycobacterium tuberculosis that resembles the phenolic glycolipid I of Mycobacterium leprae raised the prospects of a specific serodiagnostic tool for human tuberculosis. The terminal diglycosyl unit of the M. tuberculosis product was synthesized and converted to a corresponding neoglycoprotein, the O-(2,3,4-tri-O-methyl-α-L-fucopyranosyl)-(1→3)-O-α-L- rhamnopyranosyl)-(1→9)-oxynonanoyl-bovine serum albumin, and applied, in ELISA, to sera from individuals with tuberculosis. Although the correlation coefficient between the synthetic product and the native glycolipid was excellent, the seroreactivity rate of tuberculous sera was disappointing; only 24 of 119 sera from tuberculosis patients showed evidence of anti-glycolipid antibodies. In isolates of M. tuberculosis from tuberculosis patients the glycolipid was present in only 1 of 11. A partially deglycosylated version was present in two other isolates; however, most isolates lacked the glycolipid. Accordingly, while the results, unlike those of others, do not portend a future for this form of serodiagnosis in the management of tuberculosis, they offer intriguing hints as to the basis of the variable immunogenicity and pathogenicity of strains of M. tuberculosis.

AB - The report of a major triglycosyl phenol phthiocerol (phenolic) glycolipid in some strains of Mycobacterium tuberculosis that resembles the phenolic glycolipid I of Mycobacterium leprae raised the prospects of a specific serodiagnostic tool for human tuberculosis. The terminal diglycosyl unit of the M. tuberculosis product was synthesized and converted to a corresponding neoglycoprotein, the O-(2,3,4-tri-O-methyl-α-L-fucopyranosyl)-(1→3)-O-α-L- rhamnopyranosyl)-(1→9)-oxynonanoyl-bovine serum albumin, and applied, in ELISA, to sera from individuals with tuberculosis. Although the correlation coefficient between the synthetic product and the native glycolipid was excellent, the seroreactivity rate of tuberculous sera was disappointing; only 24 of 119 sera from tuberculosis patients showed evidence of anti-glycolipid antibodies. In isolates of M. tuberculosis from tuberculosis patients the glycolipid was present in only 1 of 11. A partially deglycosylated version was present in two other isolates; however, most isolates lacked the glycolipid. Accordingly, while the results, unlike those of others, do not portend a future for this form of serodiagnosis in the management of tuberculosis, they offer intriguing hints as to the basis of the variable immunogenicity and pathogenicity of strains of M. tuberculosis.

UR - http://www.scopus.com/inward/record.url?scp=0026030758&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026030758&partnerID=8YFLogxK

U2 - 10.1093/infdis/163.1.161

DO - 10.1093/infdis/163.1.161

M3 - Article

VL - 163

SP - 161

EP - 168

JO - Journal of Infectious Diseases

JF - Journal of Infectious Diseases

SN - 0022-1899

IS - 1

ER -