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Isolation of sophorose during sophorolipid production and studies of its stability in aqueous alkali: epimerisation of sophorose to 2-O-β-d-glucopyranosyl-d-mannose

机译:槐糖脂生产过程中槐糖的分离及其在碱水溶液中的稳定性研究:槐糖对2-O-β-D-吡喃葡萄糖基-d-甘露糖的差向异构化

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摘要

NMR and anion exchange chromatography analysis of the waste streams generated during the commercial production of sophorolipids by the yeast Candida bombicola identified the presence of small but significant quantities (1% w/v) of free sophorose. Sophorose, a valuable disaccharide, was isolated from the aqueous wastes using a simple extraction procedure and was purified by chromatography on a carbon celite column providing easy access to large quantities of the disaccharide. Experiments were undertaken to identify the origin of sophorose and it is likely that acetylated sophorose derivatives were produced by an enzyme catalysed hydrolysis of the glucosyl-lipid bond of sophorolipids; the acetylated sophorose derivatives then undergo hydrolysis to release the parent disaccharide.\ud\udTreatment of sophorose with aqueous alkali at elevated temperatures (0.1M NaOH at 50 °C) resulted in C2-epimerisation of the terminal reducing sugar and its conversion to the corresponding 2-O-β-d-glucopyranosyl-d-mannose which was isolated and characterised. In aqueous alkaline solution β-(1,2)-linked glycosidic bonds do not undergo either hydrolysis or peeling reactions.
机译:酵母念珠菌商业生产槐糖脂过程中产生的废物流的NMR和阴离子交换色谱分析确定存在少量但大量(1%w / v)的游离槐糖糖。槐糖,一种有价值的二糖,使用简单的提取程序从含水废物中分离出来,并通过在碳硅藻土柱上的色谱法纯化,从而易于获得大量的二糖。进行了实验以鉴定槐糖的来源,乙酰化的槐糖衍生物很可能是由酶催化的槐糖脂的糖基-脂质键水解产生的。乙酰化的槐糖糖衍生物随后进行水解以释放母体二糖。\ ud \ ud在升高的温度(50°C下0.1M NaOH)中用碱水溶液处理槐糖糖会导致末端还原糖的C2异构化并将其转化为相应的分离并表征了2-O-β-d-吡喃葡萄糖基-d-甘露糖。在碱性水溶液中,β-(1,2)-连接的糖苷键不会发生水解或剥离反应。

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