Issue 18, 2009
From the journal:

Organic & Biomolecular Chemistry

Modeling of synthetic phosphono and carba analogues of N-acetyl-α-d-mannosamine 1-phosphate, the repeating unit of the capsular polysaccharide from Neisseria meningitidis serovar A†

Lucio Toma,*a   Laura Legnani,a   Anna Rencurosi,‡b   Laura Poletti,b   Luigi Lay*b  and  Giovanni Russob  

* Corresponding authors

a Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, Pavia, Italy
E-mail: lucio.toma@unipv.it
Fax: +39 0382 987323
Tel: +39 0382 987843

b Dipartimento di Chimica Organica e Industriale and CISI, Università di Milano, Via Venezian 21, Milano, Italy
E-mail: luigi.lay@unimi.it
Fax: +39 02 50314072
Tel: +39 02 50314062

Abstract

The conformational behavior of methyl (2-acetamido-2-deoxy-α-D-mannopyranosyl)phosphate 1, and its analogues, methyl C-(2-acetamido-2-deoxy-α-D-mannopyranosyl)methanephosphonate 2 and methyl O-(2-acetamido-2-deoxy-5a-carba-α-D-mannopyranosyl)phosphate 3, where a methylene group replaces, respectively, the anomeric and the pyranose oxygen atom, was investigated at the B3LYP/6-311+G(d,p) level [6-311+G(2df,p) for the phosphorus atom]. The energy of the optimized structures was recalculated using the continuum solvent model C-PCM choosing water as the solvent. The compounds exhibited several populated conformations, but they all showed a marked preference for the 4C1 geometry of the pyranose ring; this preference was almost complete for 1, very large for the phosphono analogue 2, and large for the carba analogue 3. To give experimental support to these results, compounds 2 and 3 were synthesized and characterized by NMR spectroscopy. The comparison of the theoretical and experimental vicinal coupling constants confirmed the marked preference for the 4C1 geometry in the case of 2 and suggested that the same holds true for compound 3.

Graphical abstract: Modeling of synthetic phosphono and carba analogues of N-acetyl-α-d-mannosamine 1-phosphate, the repeating unit of the capsular polysaccharide from Neisseria meningitidis serovar A

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B907000A
Article type
Paper
Submitted
07 Apr 2009
Accepted
15 Jun 2009
First published
10 Jul 2009

Org. Biomol. Chem., 2009,7, 3734-3740

Permissions

Request permissions

Modeling of synthetic phosphono and carba analogues of N-acetyl-α-D-mannosamine 1-phosphate, the repeating unit of the capsular polysaccharide from Neisseria meningitidis serovar A

L. Toma, L. Legnani, A. Rencurosi, L. Poletti, L. Lay and G. Russo, Org. Biomol. Chem., 2009, 7, 3734 DOI: 10.1039/B907000A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements