ChemComm
DOI: 10.1039/C5CC03P74a6gHe 4 of 4
COMMUNICATION
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the previously reported “substrate engineering” strategy,21 this
approach excluded chemical protection/deprotection steps.
R. Bertozzi, G. W. Hart and M. E. Etzler, New York, 2nd edn., 2009, ch.
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Table 3. Synthesis of di-sialyl GNB derivatives via the one-pot two-
enzyme 2–6-sialylation system shown in Scheme 3.
Acceptors
Products
Yields (%)
6
7
8
9
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25
81
28
Neu5Ac2–3Gal6deoxy1–3(Neu5Ac2–6)GalNAc
26
27
57
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29 Neu5Ac2–3GalA1–3(Neu5Ac2–6)GalNAc
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In summary, taking advantages of the acceptor substrate
promiscuity of BiGalK and donor substrate promiscuity of
BiGalHexNAcP, various novel GNB and LNB derivatives were
synthesized using an efficient one-pot two-enzyme system. These
compounds were used for acceptor substrate specificity study of
PmST1 and efficient synthesis of sialyl GNB derivatives. Finally,
well-controlled synthesis of di-sialyl GNB was achieved by
selectively blocking one of the C6-glycosylation sites on
Gal/GalNAc in the substrates. The compounds synthesized in this
study are valuable probes for elucidating the biological roles of
GNB, sialyl and di-sialyl GNB-containing glycans.
This work was supported by National Natural Science
Foundation of China grant 31100587 (to L. Li), as well as
National Institute of Health grants R01 GM085267 (to P.G.
Wang) and R01 HD065122 (to X. Chen).
Notes and references
a
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Angew Chem Int Ed Engl, 2006, 45, 3938.
21 X. Meng, W. Yao, J. Cheng, X. Zhang, L. Jin, H. Yu, X. Chen, F. Wang
and H. Cao, J Am Chem Soc, 2014, 136, 5205.
Department of Chemistry and Center for Diagnostics & Therapeutics,
Georgia State University, Atlanta, GA 30303, USA. E-mail:
b
State Key Laboratory of Medicinal Chemical Biology and College of
Pharmacy, Nankai University, Tianjin 300071, PR China.
c
Department of Chemistry, University of California, Davis, One Shields
Avenue, Davis, CA 95616, USA.
†
Electronic Supplementary Information (ESI) available: Experimental
details for substrate specificity study and enzymatic synthesis, NMR and
HRMS data and spectra. See DOI: 10.1039/c000000x/
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