~(13)C标记和未标记果糖化赖氨酸“一釜法”合成工艺的研究
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摘要
为了能够快速、高效合成果糖化赖氨酸及其~(13)C同位素标记物,分别以~(13)C同位素标记、非标记的葡萄糖和Fmoc保护赖氨酸为原料,通过对阿马德里反应与Fmoc脱除反应的工艺条件进行系统优化,建立了串联"一釜法"合成工艺。该方法大幅提升了果糖化赖氨酸的合成效率,为实现果糖化赖氨酸的工业化生产奠定了基础。
This research reported a tandem one-pot procedure for rapidly and efficiently constructing the fructosyl-lysine and the ~(13)C labeled derivatives by optimizing the synthetic conditions of Amadori reaction and deprotection reaction.This process using non-labeled and ~(13)C labeled glucose and Fmoc-lysine as the starting materials,which could not only improve the synthetic efficiency of fructosyl-lysine and its derivatives,but also could provide the basis for the industrial manufacture.
This research reported a tandem one-pot procedure for rapidly and efficiently constructing the fructosyl-lysine and the ~(13)C labeled derivatives by optimizing the synthetic conditions of Amadori reaction and deprotection reaction.This process using non-labeled and ~(13)C labeled glucose and Fmoc-lysine as the starting materials,which could not only improve the synthetic efficiency of fructosyl-lysine and its derivatives,but also could provide the basis for the industrial manufacture.
引文
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[2]Vinale F,Fogliano V,Schieberle P,et al.Development of a stable isotope dilution assay for an accurate quantification of protein-bound N(epsilon)-(1-deoxyD-fructos-1-yl)-L-lysine using a(13)C-labeled internal standard[J].Journal of Agricultural&Food Chemistry,1999,47(12):5084-5092.
[3]Roohk H V,Zaidi A R.A review of glycated albumin as an intermediate glycation index for controlling diabetes[J].Journal of Diabetes Science&Technology,2008,2(6):1114-1121.
[4]陈浩,田恒力,戎伯英,等.脑外伤急性期空腹血糖、血清糖化白蛋白和乳酸脱氢酶联合检测的意义[J].上海交通大学学报(医学版),2007,27(12):1478-1480.
[5]Takei I,Hoshino T,Tominaga M,et al.Committee on Diabetes Mellitus Indices of the Japan Society of Clinical Chemistry-recommended reference measurement procedure and reference materials for glycated albumin determination[J].Annals of Clinical Biochemistry,2016,53(1):124-132.
[6]薛菲,彭效明,李翠清,等.离子液体辅助提取葡萄籽中原花青素的工艺研究[J].北京石油化工学院学报,2017,25(3):1-6.
[7]王敏,潘鹤,姜宏旭,等.氯化亚锡催化“一锅法”合成N1-取代的3,4-二氢嘧啶-2(1H)-酮[J].化学通报,2017,80(9):863-867.
[8]李军,杨天宇,张怀远,等.铟粉促进下“一锅法”合成三氟甲基高烯丙基酰肼化合物[J].有机化学,2017,37(4):925-935.
[9]彭家建,邓友全.室温离子液体催化“一锅法”合成3,4-二氢嘧啶-2-酮[J].有机化学,2002,22(1):71-72.
[10]冯忖,李惠,毛春晖,等.一锅法合成2,3-二氯吡啶[J].精细化工中间体,2008,38(5):19-21.
[11]Alexey K,Vladimir G.General and Practical OnePot Synthesis of Dihydrobenzosiloles from Styrenes[J].Cheminform,2012,14(3):914-917.
[12]Suchand B,Satyanarayana G.Palladium-catalyzed acylations:one-pot synthesis of indenones[J].Journal of Organic Chemistry,2017,82(1):372-381.
[13]Gavin C T,Jennifer T,Patrick D,et al.One-pot synthesis of chiral dihydrobenzofuran framework via Rh/Pd catalysis[J].Organic Letters,2012,14(21):5542-5545.
[14]Bogolubsky A V,MorozY S,Mykhailiuk P K,et al.One-pot parallel synthesis of alkyl sulfides,sulfoxides,sulfones[J].Acs Combinatorial Science,2015,17(6):348-354.
[15]周亚斌,史铁钧,任强,等.一锅法乳液聚合制备聚苯乙烯/蒙脱土纳米复合材料[J].高分子材料科学与工程,2005,21(1):125-128.