Solid-phase synthesis of N-trichloroacetyl mannosamine 1-phosphate repeating units mimicking capsular polysaccharide derived from Neisseria meningitidis serotype A

N-Trichloroacetyl analogs of N-acetylmannosamine 1-phosphate repeating units, which are found in capsular polysaccharides of Neisseria meningitidis serotype A, were successfully obtained via solid-phase synthesis using an oxazaphospholidine monomer. The introduction of the trichloroacetyl group into...

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Bibliographic Details
Published in:Carbohydrate research 2022-08, Vol.518, p.108585-108585, Article 108585
Main Authors: Sato, Kazuki, Chiba, Akie, Shiraishi, Tomomi, Ogawa, Yuki, Hara, Rintaro Iwata, Wada, Takeshi
Format: Article
Language:English
Subjects:
Glycosyl phosphate
Neisseria meningitidis
Oxazaphospholidine
Solid-phase synthesis
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Summary:N-Trichloroacetyl analogs of N-acetylmannosamine 1-phosphate repeating units, which are found in capsular polysaccharides of Neisseria meningitidis serotype A, were successfully obtained via solid-phase synthesis using an oxazaphospholidine monomer. The introduction of the trichloroacetyl group into the amino group of mannosamine resulted in the stabilization of the reaction intermediates. Monosaccharide, disaccharide, and tetrasaccharide derivatives were obtained and isolated. This is the first example to demonstrate the synthesis of the N-acylated mannosamine 1-phosphate structure having no less than four phosphate linkages. [Display omitted] •N-Trichloroacetyl analogs of N-acetylmannosamine 1-phosphate repeating units were obtained.•Solid-phase synthesis using an oxazaphospholidine monomer was conducted.•Trichloroacetyl group stabilized the reaction intermediates.•Monosaccharide, disaccharide, and tetrasaccharide derivatives were obtained and isolated.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2022.108585