MECHANISM OF FORMATION OF CHLOROPROPANOLS PRESENT IN PROTEIN HYDROLYSATES
MECHANISM OF FORMATION OF CHLOROPROPANOLS PRESENT IN PROTEIN HYDROLYSATES
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DOI：
10.1007/bf02662173
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发表时间：
1991-10-01
影响因子：
2
通讯作者：
DAVIES, AP
中科院分区：
文献类型：
--
作者：
COLLIER, PD;CROMIE, DDO;DAVIES, AP
氯丙醇是通过盐酸与生产中使用的蛋白质材料相关的残留脂质反应而在蛋白质水解产物中形成的。通过薄层色谱和气相色谱分析了甘油、三油酸甘油酯、1,2-二酰基-sn-甘油-3-磷酰胆碱和豆粕形成的产物。所形成的氯丙二醇和二氯丙醇的产率和异构体比率根据其形成的反应机制来解释，其中涉及氯阴离子在邻近酯基团活化的位置处的优先亲核取代。它们提供嵌合协助并通过空间和电子效应控制区域选择性。
Chloropropanols are formed in protein hydrolysates by the reaction of hydrochloric acid with residual lipids associated with the proteinaceous materials used in their production. The products formed from glycerol, triolein, 1,2-diacyl-sn-glycero-3-phosphorylcholine and soya meal have been analyzed by thin-layer and gas chromatography. The yields and isomer ratios of the chloropropandiols and dichloropropanols formed are interpreted in terms of reaction mechanisms for their formation, which involve preferential nucleophilic substitution by the chloride anion at positions activated by neighboring ester groups. These provide anchimeric assistance and govern regioselectivity through steric and electronic effects.