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 Jun 5;17(11):2642-5.
doi: 10.1021/acs.orglett.5b01013. Epub 2015 May 8.

Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan

Shu-Lun Tang  1 , Nicola L B Pohl  1   2
Affiliations

Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan

Shu-Lun Tang et al. Org Lett. .

Abstract

The first automated solution-phase synthesis of β-1,4-mannuronate and β-1,4-mannan oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, β-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the β-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to β-mannan synthesis.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Retrosynthetic Strategy
Scheme 2
Scheme 2. Synthesis of the Building Block 6 for the Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan Hexamers
Scheme 3
Scheme 3. Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan Hexamers
Scheme 4
Scheme 4. Deprotection of β-1,4-Mannuronate Hexamer 9 and β-1,4-Mannan Hexamer 10
See this image and copyright information in PMC

References

    1. Heuckendorff M.; Bendix J.; Pedersen C. M.; Bols M. Org. Lett. 2014, 16, 1116–1119. - PubMed
    2. Baek J. Y.; Lee B.-Y.; Jo M. G.; Kim K. S. J. Am. Chem. Soc. 2009, 131, 17705–17713. - PubMed
    3. Stork G.; La Clair J. J. J. Am. Chem. Soc. 1996, 118, 247–248.
    4. Wu X.; Bundle D. R. J. Org. Chem. 2005, 70, 7381–7388. - PubMed
    1. Gamblin D. P.; Scanlan E. M.; Davis B. G. Chem. Rev. 2009, 109, 131–163. - PubMed
    2. Schmaltz R. M.; Hanson S. R.; Wong C.-H. Chem. Rev. 2011, 111, 4259–4307. - PubMed
    1. Crich D.; Li H.; Yao Q.; Wink D. J.; Sommer R. D.; Rheingold A. L. J. Am. Chem. Soc. 2001, 123, 5826–5828. - PubMed
    2. Crich D.; Banerjee A.; Yao Q. J. Am. Chem. Soc. 2004, 126, 14930–14934. - PubMed
    1. Nitz M.; Purse B. W.; Bundle D. R. Org. Lett. 2000, 2, 2939–2942. - PubMed
    2. Nitz M.; Bundle D. R. J. Org. Chem. 2001, 66, 8411–8423. - PubMed
    3. Wu X.; Bundle D. R. J. Org. Chem. 2005, 70, 7381–7388. - PubMed
    1. Walters K. R. Jr.; Serianni A. S.; Sformo T.; Barnes B. M.; Duman J. G. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 20210–20215. - PMC - PubMed
    2. Ishiwata A.; Sakurai A.; Nishimiya Y.; Tsuda S.; Ito Y. J. Am. Chem. Soc. 2011, 133, 19524–19535. - PubMed
    3. Crich D.; Rahaman M. Y. J. Org. Chem. 2011, 76, 8611–8620. - PMC - PubMed

Publication types