Host Sialic Acids: A Delicacy for the Pathogen with Discerning Taste.
Host Sialic Acids: A Delicacy for the Pathogen with Discerning Taste.
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DOI：
10.1128/microbiolspec.mbp-0005-2014
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发表时间：
2015-08
影响因子：
3.7
通讯作者：
Boyd EF
中科院分区：
文献类型：
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作者：
Haines-Menges BL;Whitaker WB;Lubin JB;Boyd EF
唾液酸（神经氨酸）是一个由九个碳（非酮糖）α-酮酸性碳水化合物组成的多样化家族。典型的唾液酸，2-酮基-3-脱氧-5-乙酰氨基-D-甘油基-D-半乳糖基-壬酮糖酸，也称为N-乙酰神经氨酸（Neu 5Ac），是进行大量已知修饰的骨架（1）。Neu 5Ac结构的典型特征是具有甘油尾、C-5位的乙酰氨基和C-4、C-7、C-8和C-9上存在的羟基的6碳羧酸环结构。修饰主要发生在羟基上，其中O-乙酰化是最常见的改变，并且取代已被证明在核心结构完成后发生（2）。其他修饰阿索-甲基化、O-乳酸化和O-硫酸化增加了该分子在体内的多样性。自然界中也存在两种结构相似的唾液酸，N-羟乙酰神经氨酸（Neu 5Gc），其与Neu 5Ac的不同之处在于N-5乙酰基部分上存在羟基，以及2-酮基-3-脱氧-D-甘油基-D-半乳糖基-壬酮糖酸（KDN），Neu 5Ac的脱氨基形式，并且对其核心结构进行了类似的修饰（1）。这三种主要结构（Neu 5Ac、Neu 5Gc和KDN）包含唾液酸家族，因为它们保留了相同的9碳骨架立体化学构型。
Sialic acids (neuraminic acids) are a diverse family of nine carbon (nonulosonic) α‐keto acidic carbohydrates. The canonical sialic acid, 2‐keto‐3‐deoxy‐5‐acetamido‐D‐glycero‐D‐galacto‐nonulosonic acid, also known asN‐acetylneuraminic acid (Neu5Ac) is the backbone on which a large number of known modifications are made (1). The Neu5Ac structure is typified by a 6‐carbon carboxylic acid ring structure with a glycerol tail, an acetamido at the C‐5 position and hydroxyl groups present on C‐4, C‐7, C‐8, and C‐9. Modifications occur primarily on the hydroxyl groups, withO‐acetylation being the most common alteration, and substitutions have been shown to occur after the completion of the core structure (2). Other modifications such asO‐methylation,O‐lactylation, andO‐sulfation add to the diversity of this moleculein vivo. Two structurally similar sialic acids,N‐glycolylneuraminic acid (Neu5Gc), which differs from Neu5Ac by the presence of a hydroxyl group on the N‐5 acetyl moiety, and 2‐keto‐3‐deoxyl‐D‐glycero‐D‐galacto‐nonulosonic acid (KDN), a deaminated form of Neu5Ac, also occur in nature and similar modifications are made to their core structure (1). These three main structures (Neu5Ac, Neu5Gc, and KDN) encompass the family of sialic acids due to their retention of the same stereochemical configuration of the 9‐carbon backbone.