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. 2012 Feb 3;77(3):1449-56.
doi: 10.1021/jo202322k. Epub 2012 Jan 12.

Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Sayaka Masuko  1 , Smritilekha Bera, Dixy E Green, Michel Weïwer, Jian Liu, Paul L DeAngelis, Robert J Linhardt
Affiliations

Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Sayaka Masuko et al. J Org Chem. .

Abstract

Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

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Figures

Figure 1
Figure 1
Enzymatic synthesis of UDP-GlcNAc and UDP-GalNAc analogs
Scheme 1
Scheme 1
Synthesis of GlcNH2-1-phosphate
Scheme 2
Scheme 2
Synthesis of GlcNAc/GalNAc-1-phosphate
Scheme 3
Scheme 3
Synthesis of GlcN-alkyne-1-phosphate
Scheme 4
Scheme 4
Synthesis of GalN-alkyne-1-phosphate
Scheme 5
Scheme 5
GlcN-TFA-1-phosphate
Scheme 6
Scheme 6
Synthesis of GlcN-ene-1-phosphate
Scheme 7
Scheme 7
Chemical synthesis of UDP-GlcN derivatives
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