The Experimental Evidence in Support of Glycosylation Mechanisms at the S(N)1-S(N)2 Interface.
The Experimental Evidence in Support of Glycosylation Mechanisms at the S(N)1-S(N)2 Interface.
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DOI：
10.1021/acs.chemrev.8b00083
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发表时间：
2018-09-12
期刊：
影响因子：
62.1
通讯作者：
Crich D
中科院分区：
文献类型：
--
作者：
Adero PO;Amarasekara H;Wen P;Bohé L;Crich D
提供了支持糖基化反应机制的最新证据的重要综述。影响假定的oxocarbenium离子作为中间体在SN 1端的机械连续的稳定性的因素首先调查之前的证据，光谱和间接，糖基化反应的时间尺度上存在这样的物种。当前模型的非对映选择性在亲核攻击oxocarbenium离子。证据支持的中间活化的共价糖基捐助者进行审查，亲核试剂的结构，溶剂，温度的影响之前，和供体-受体氢键的糖基化反应的机制进行调查。糖基化反应的动力学研究和使用动力学同位素效应的过渡态结构的测定，计算模型之前，最后调查。审查的结论是对最新技术的批判性评价。
A critical review of the state-of-the-art evidence in support of the mechanisms of glycosylation reactions is provided. Factors affecting the stability of putative oxocarbenium ions as intermediates at the SN1 end of the mechanistic continuum are first surveyed before the evidence, spectroscopic and indirect, for the existence of such species on the timescale of glycosylation reactions is presented. Current models for diastereoselectivity in nucleophilic attack on oxocarbenium ions are then described. Evidence in support of the intermediacy of activated covalent glycosyl donors is reviewed, before the influence of the structure of the nucleophile, of the solvent, of temperature, and of donor-acceptor hydrogen bonding on the mechanism of glycosylation reactions are surveyed. Studies on the kinetics of glycosylation reactions and the use of kinetic isotope effects for the determination of transition state structure are presented, before computational models are finally surveyed. The review concludes with a critical appraisal of the state of the art.
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影响因子：
2
作者：
Balmond, Edward I.;Galan, M. Carmen;McGarrigle, Eoghan M.
通讯作者：
McGarrigle, Eoghan M.
影响因子：
15
作者：
BENNET, AJ;SINNOTT, ML
通讯作者：
SINNOTT, ML
影响因子：
2.7
作者：
Bols M;Pedersen CM
通讯作者：
Pedersen CM
影响因子：
3.1
作者：
Bohe, Luis;Crich, David
通讯作者：
Crich, David
影响因子：
1.8
作者：
BOZO, E;VASELLA, A
通讯作者：
VASELLA, A