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. 2013 Nov 4;52(45):11852-6.
doi: 10.1002/anie.201305667. Epub 2013 Sep 13.

Tailored design and synthesis of heparan sulfate oligosaccharide analogues using sequential one-pot multienzyme systems

Yi Chen  1 , Yanhong Li, Hai Yu, Go Sugiarto, Vireak Thon, Joel Hwang, Li Ding, Liana Hie, Xi Chen
Affiliations

Tailored design and synthesis of heparan sulfate oligosaccharide analogues using sequential one-pot multienzyme systems

Yi Chen et al. Angew Chem Int Ed Engl. .
No abstract available

Keywords: carbohydrates; chemoenzymatic systems; enzymes; heparin; structure-activity relationships.

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Figures

Scheme 1
Scheme 1
Sequential one-pot multienzyme (OPME) chemoenzymatic synthesis of heparan sulfate (HS) oligosaccharide analogs. GlyK, glycokinase; NucT, monosaccharide-1-phosphate nucleotidyltransferase; PpA, inorganic pyrophosphatase; GlyT, glycosyltransferase.
Scheme 2
Scheme 2
One-pot four-enzyme GlcNAc activating and transfer system for the synthesis of GlcNAcα1–4GlcAβ2AA disaccharide and derivatives. Tris-HCl buffer (100 mM, pH 7.5) was used for the synthesis of disaccharides 5 and 7 and MES buffer (100 mM, pH 6.5) was used for the synthesis of disaccharide 6. NahK_ATCC55813, Bifidobacterium longum ATCC55813 N-acetylhexosamine 1-kinase; PmGlmU, Pasteurella multocida strain P-1059 (ATCC15742) N-acetylglucosamine-1-phosphate uridylyltransferase; PmPpA, Pasteurella multocida strain P-1059 inorganic pyrophosphatase; PmHS2, Pasteurella multocida strain P-1059 heparosan synthase 2.
Scheme 3
Scheme 3
PmHS2-catalyzed synthesis of GlcNAcα1–4GlcAβ2AA disaccharide derivatives 11–13 in Tris-HCl buffer (100 mM, pH 7.5).
Scheme 4
Scheme 4
One-pot three-enzyme GlcA activation and transfer system for the synthesis of GlcAβ1–4GlcNAcα1–4GlcAβ2AA trisaccharide and derivatives. EcGalU, Escherichia coli K-12 glucose-1-phosphate uridylyltransferase; PmUgd, Pasteurella multocida strain P-1059 UDP-glucose dehydrogenase.
Scheme 5
Scheme 5
One-pot four-enzyme synthesis of tetrasaccharide 20 and subsequent chemical derivatization reactions for the formation of tetrasaccharides 21–24. Reagents and conditions: (a) K2CO3, H2O, r.t. overnight, 81%; (b) complex Py•SO3, 2 M NaOH, H2O, 3 days, 70%; (c) H2, Pd/C, MeOH, H2O, 1 h, quantitative.
Scheme 6
Scheme 6
Structural comparison of Fondaparinux (Arixtra) and Idraparinux. Differences are underlined.
See this image and copyright information in PMC

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