L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues.,Organic & Biomolecular Chemistry

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L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-01-08 , DOI: 10.1039/c9ob02476j
John B McArthur ₁ , Abhishek Santra ₁ , Wanqing Li ₁ , Anoopjit S Kooner ₁ , Ziqi Liu ₁ , Hai Yu ₁ , Xi Chen ₁

Affiliation

5,7-Di-N-acetyllegionaminic acid (Leg5,7Ac2) is a bacterial nonulosonic acid (NulO) analogue of sialic acids, an important class of monosaccharides in mammals and in some bacteria. To develop efficient one-pot multienzyme (OPME) glycosylation systems for synthesizing Leg5,7Ac2-glycosides, Legionella pneumophila cytidine 5'-monophosphate (CMP)-Leg5,7Ac2 synthetase (LpCLS) was cloned and characterized. It was successfully used in producing Leg5,7Ac2-glycosides from chemoenzymatically synthesized Leg5,7Ac2 using a one-pot two-enzyme system or from its chemically synthesized six-carbon monosaccharide precursor 2,4-diacetamido-2,4,6-trideoxymannose (6deoxyMan2,4diNAc) in a one-pot three-enzyme system. In addition, LpCLS was shown to tolerate Neu5Ac7NAc, a C9-hydroxyl analogue of Leg5,7Ac2 and also a stable analogue of 7-O-acetylneuraminic acid (Neu5,7Ac2), to allow OPME synthesis of the corresponding α2-3-linked sialosides, from chemically synthesized six-carbon monosaccharide precursor 4-N-acetyl-4-deoxy-N-acetylmannosamine (ManNAc7NAc).

中文翻译：

肺炎链球菌CMP-5,7-二-N-乙酰基硫代氨基甲酸合成酶（LpCLS）参与了唾液酸苷和类似物的化学酶法合成。

5,7-二-N-乙酰基硫磺酰胺酸（Leg5,7Ac2）是唾液酸的细菌壬二酸（NulO）类似物，是哺乳动物和某些细菌中的一类重要的单糖。为了开发用于合成Leg5,7Ac2-糖苷的高效一锅多酶（OPME）糖基化系统，克隆并鉴定了嗜肺军团杆菌胞苷5'-单磷酸酯（CMP）-Leg5,7Ac2合成酶（LpCLS）。它已成功用于通过一锅两酶系统由化学酶法合成的Leg5,7Ac2或其化学合成的六碳单糖前体2,4-二乙酰氨基-2,4,6-三脱氧甘露糖（一锅三酶系统中的6deoxyMan2,4diNAc）。此外，LpCLS还可以耐受Neu5Ac7NAc（Leg5的C9-羟基类似物），

更新日期：2020-02-10

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