Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2015 Feb 20;17(4):928-31.
doi: 10.1021/acs.orglett.5b00031. Epub 2015 Feb 6.

Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization

Ivan A Gagarinov  1 , Tao Fang, Lin Liu, Apoorva D Srivastava, Geert-Jan Boons
Affiliations

Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization

Ivan A Gagarinov et al. Org Lett. .

Abstract

The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging α-fucosylation and β-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a β-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Retrosynthetic analysis.
Scheme 1
Scheme 1
Attempted Assembly of Trisaccharide 6
Scheme 2
Scheme 2
Improved Assembly of Target Trisaccharide 4
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Daum RS, Spellberg B. Clin. Infect. Dis. 2012;54:560–567. - PMC - PubMed
    1. Lowy FD. New Engl. J. Med. 1998;339:520–532. - PubMed
    2. Fridkin SK, Hageman JC, Morrison M, Sanza LT, Como-Sabetti K, Jernigan JA, Harriman K, Harrison LH, Lynfield R, Farley MM. New Engl. J. Med. 2005;352:1436–1444. - PubMed
    1. Chambers HF, DeLeo FR. Nat. Rev. Microbiol. 2009;7:629–641. - PMC - PubMed
    1. O'Riordan K, Lee JC. Clin. Microbiol. Rev. 2004;17:218–234. - PMC - PubMed
    1. Jones C. Carbohydr. Res. 2005;340:1097–1106. - PubMed

Publication types

MeSH terms

LinkOut - more resources