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Critical approaches in the catalytic transformation of sugar isomerization and epimerization after Fischer-History,challenges,and prospects

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Green Energy & Environment 2024年第3期9卷 435-453页

作者： Da-Ming Gao Xun Zhang Haichao Liu Hidemi Fujino Tingzhou Lei Fuan Sun Jie Zhu Taoli Huhe National-local Joint Engineering Research Center of Biomass Refine and High-Quality Utilization Changzhou UniversityChangzhou213164China Institute of Urban and Rural Mining Research Changzhou UniversityChangzhou213164China Changzhou Key Laboratory of Biomass Green Safe&High Value UtilizationChangzhou UniversityChangzhou213164China Beijing National Laboratory for Molecular Science College of Chemistry and Molecular EngineeringPeking UniversityBeijing100871China Department of Rehabilitation Science Kobe University Graduate School of Health SciencesKobe654-0142Japan

The transformation of aldose to ketose or common sugars into rare saccharides,including rare ketoses and aldoses,is of great value and interest to the food industry and for saccharidic biomass utilization,medicine,and the synthesis of ***,high-fructose corn syrup(HFCS)is industrially produced in more than 10 million tons annually using immobilized glucose *** low-calorie saccharides such as tagatose and psicose,which are becoming popular sweeteners,have also been produced on a pilot scale in order to replace sucrose and ***,current catalysts and catalytic processes are still difficult to utilize in biomass conversion and also have strong substrate dependence in producing high-value,rare *** the specific reaction properties of saccharides and catalysts,since the pioneering discovery by Fischer,various catalysts and catalytic systems have been discovered or developed in attempts to extend the reaction pathways,improve the reaction efficiency,and to potentially produce commercial *** this review,we trace the history of sugar isomerization/epimerization reactions and summarize the important breakthroughs for each reaction as well as the difficulties that remain unresolved to date.

关键词： Rare sugars Isomerization Ketonization epimerization Catalytic transformation

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Anomeric configuration-dependence of the Lattrell-Dax epimerization from D-glucose to synthetically useful D-allose derivatives

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Chinese Journal of Natural Medicines 2020年第10期18卷 723-728页

作者： NING Yun-Zhan QIN Chun-Jun SUN Wen-Bin FU Jun-Jie HU Jing YIN Jian Key Laboratory of Carbohydrate Chemistry and Biotechnology Ministry of EducationSchool of BiotechnologyJiangnan UniversityWuxi 214122China Wuxi School of Medicine Jiangnan UniversityWuxi 214122China

D-Allose and its derivatives play important roles in the field of health care and food nutrition. Pure and well-defined Dallose derivatives can facilitate the elucidation of their structure-activity relationship as an essential step for drug design. The LattrellDax epimerization, refers to the triflate inversion using nitrite reagent, is known as valuable method for the synthesis of rare D-allose derivatives. Here, the influence of protecting group patterns on the transformation efficiency of D-glucose derivatives into synthetically useful D-alloses and D-allosamines via the Lattrell-Dax epimerization was studied. For C3 epimerization of D-glucose derivatives bearing O2-acyl group, an anomeric configuration-dependent acyl migration from O2 to O3 was found. In addition, a neighbouring group participation effect-mediated SN1 nucleophilic substitution of the D-glucosamine bearing C2 trichloroacetamido(TCA) group in the Lattrell-Dax epimerization was dependent upon anomeric configuration. Thus, the effect of anomeric configuration on the LattrellDax epimerization of D-glucose suggests that β-D-glucosides with low steric hindrance at C2 should be better substrates for the synthesis of D-allose derivatives. Significantly, the efficient synthesis of the orthogonally protected D-allose 13 and D-allosamine 18 will serve well for further assembly of complex glycans.

关键词： D-allose D-allosamine epimerization Anomeric configuration Acyl migration

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Hydrolysis Reactions and Resolution of (±)-2-Acetamido-3-hydroxy-1-(4-nitrophenyl)-1-propanone

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Chemical Research in Chinese Universities 2002年第4期18卷 409-411页

作者： YANG Hui QIU Guo-fu FENG Xichun HE Jian-she HU Xian-ming College of Pharmacy Wuhan UniversityWuhan 430072P.R.China

The hydrolysis reaction of (±)-2-acetamido-3-hydroxy-1-(4-nitrophenyl)-1-propanone[(±)-[STHZ]1], an intermediate of chloramphenicol, was studied and three different products were obtained respectively under different reaction conditions. The resolution of hydrolysis product (±)-2-amino-3-hydroxy- 1-(4-nitrophenyl)-1-propanone, an intermediate of chloramphenicol, was studied and three different products were obtained respectively under different reaction conditions. The resolution of hydrolysis product (±)-2-amino-3-hydroxy- 1-(4-nitrophenyl)-1-propanone[(±)-[STHZ]3] was carried out. A process of crystallization-induced asymmetric transformation was observed and up to 76% of the optically pure enantiomer was obtained in the resolution of (±)- was carried out. A process of crystallization-induced asymmetric transformation was observed and up to 76% of the optically pure enantiomer was obtained in the resolution of (±)-3.

关键词： Hydrolysis Resolution epimerization

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Indole methylation protects diketopiperazine configuration in the maremycin biosynthetic pathway

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Science China Chemistry 2016年第9期59卷 1224-1228页

作者： Yingxia Lan Yi Zou Tingting Huang Xiaozheng Wang Nelson L. Brock Zixin Deng Shuangjun Lin State Key Laboratory of Microbial Metabolism:Joint International Laboratory on Metabolic & Developmental Sciences School of Life Sciences & Biotechnology Shanghai Jiao Tong University Shanghai 200030 China

The maremycin biosynthetic gene cluster has been identified in Streptomyces sp. B9173. Comparative metabolic profiling with knockout mutant strains led to the identification of new products correlated to the maremycin biosynthesis, in particular the ＂demethyl＂-maremycins with an unexpected D-tryptophan unit. A biosynthetic pathway for the maremycins is proposed and plausible reasoning for tryptopban epimerization in the demethylmaremycin biosynthesis is also provided.

关键词： biosynthesis maremycin N-methylation methyltransferase epimerization

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