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. 2015 Mar 18;51(22):4595-8.
doi: 10.1039/c4cc10306h.

Improved one-pot multienzyme (OPME) systems for synthesizing UDP-uronic acids and glucuronides

Musleh M Muthana  1 , Jingyao Qu, Mengyang Xue, Timofey Klyuchnik, Alex Siu, Yanhong Li, Lei Zhang, Hai Yu, Lei Li, Peng G Wang, Xi Chen
Affiliations

Improved one-pot multienzyme (OPME) systems for synthesizing UDP-uronic acids and glucuronides

Musleh M Muthana et al. Chem Commun (Camb). .

Abstract

Arabidopsis thaliana glucuronokinase (AtGlcAK) was cloned and shown to be able to use various uronic acids as substrates to produce the corresponding uronic acid-1-phosphates. AtGlcAK or Bifidobacterium infantis galactokinase (BiGalK) was used with a UDP-sugar pyrophosphorylase, an inorganic pyrophosphatase, with or without a glycosyltransferase for highly efficient synthesis of UDP-uronic acids and glucuronides. These improved cost-effective one-pot multienzyme (OPME) systems avoid the use of nicotinamide adenine dinucleotide (NAD(+))-cofactor in dehydrogenase-dependent UDP-glucuronic acid production processes and can be broadly applied for synthesizing various glucuronic acid-containing molecules.

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Figures

Scheme 1
Scheme 1
A one-pot multienzyme (OPME) strategy for chemoenzymatic synthesis of uronosides. GlyK, glycokinase; USP, UDP-sugar pyrophosphorylase; PmPpA, Pasteurella multocida inorganic pyrophosphatase; UAT, uronosyltransferase. D-GlcA (1), GlcA-1-P (5), and UDP-GlcA (9): R1 = R3 = OH, R2 = R4 = R6 = H, R5 = CO2H; D-GalA (2), GalA-1-P (6), and UDP-GalA (10): R1 = R4 = OH, R2 = R3 = R6 = H, R5 = CO2H; D-ManA (3), ManA-1-P (7), and UDP-ManA (11): R2 = R3 = OH, R1 = R4 = R6 = H, R5 = CO2H; L-IdoA (4), IdoA-1-P (8), and UDP-IdoA (12): R1 = R3 = OH, R2 = R4 = R5 = H, R6 = CO2H.
Scheme 2
Scheme 2
Sequential OPME synthesis of heparosan disaccharide (14), trisaccharide (15), and tetrasaccharide (16). Enzymes used: NahK, N-acetylhexosamine-1-phosphate kinase; PmGlmU, Pasteurella multocida N-acetylglucosamine-1-phosphate uridylyltransferase; PmPpA, Pasteurella multocida inorganic pyrophosphatase; PmHS2, Pasteurella multocida heparosan synthase 2; AtGlcAK, Arabidopsis thaliana glucuronokinase; BLUSP, Bifidobacterium longum UDP-sugar pyrophosphorylase.
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