Organic Letters
Letter
and using Et N as the base. Thus the Manβ(1−4)GlcNAc
Author
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2
1
disaccharide 14a was converted into pPNP glycoside 14b in
9% yield, whereas diacetylchitobiose 15a gave 15b in 65%
yield.
Finally, as a demonstration that the process could be applied
to large oligosaccharide structures, the complex biantennary
Xin Qiu − School of Physical and Chemical Sciences, University
of Canterbury, Christchurch 8140, New Zealand
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22
sialyl glycan (SG) decasaccharide 16a, isolated from egg
yolks, was converted into the corresponding pNP glycoside
Notes
The authors declare no competing financial interest.
16b in 75% isolated yield (isolated as its ammonium salt,
Scheme 1). pNP glycoside 16b was then demonstrated to be a
ACKNOWLEDGMENTS
We thank the Biomolecular Interaction Center at the
University of Canterbury for financial support.
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Scheme 1. Direction Conversion of a Complex Bi-antennary
SG Decasaccharide into the Corresponding pNP Glycoside
REFERENCES
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ENGase) Endo M. (See Figure S1.) This final example
demonstrates the utility of the process for the direct conversion
of complex oligosaccharides isolated from natural sources
directly into the corresponding pNP glycosides without any
protecting group chemistry and the production of complex
enzyme substrates in a single step.
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ASSOCIATED CONTENT
sı Supporting Information
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ization and spectra (PDF)
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11−19.
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(22) Umekawa, M.; Higashiyama, T.; Koga, Y.; Tanaka, T.;
Noguchi, M.; Kobayashi, A.; Shoda, S.-I.; Huang, W.; Wang, L.-X.;
Antony J. Fairbanks − School of Physical and Chemical Sciences
Ashida, H. Biochim. Biophys. Acta, Gen. Subj. 2010, 1800, 1203−1209.
(23) Fairbanks, A. J. Chem. Soc. Rev. 2017, 46, 5128−5146.
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