Enzymes in Organic Synthesis, 15 (∞) Short Enzymatic Synthesis of l-Fucose Analogs
Enzymes in Organic Synthesis, 15 (∞) Short Enzymatic Synthesis of l-Fucose Analogs
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有机合成中的酶，15 (∞) L-岩藻糖类似物的短酶法合成
DOI：
10.1002/chin.200012237
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发表时间：
2000
期刊：
影响因子：
--
通讯作者：
O. Eyrisch
中科院分区：
文献类型：
--
作者：
W. Fessner;G. Jaeschke;O. Eyrisch
报道了一种合成非极性末端修饰的 L-岩藻糖类似物的短酶促路线。特别是，已经制备了带有延伸的直链(1b)和支链(1e)饱和或各种不饱和(1c，1d)脂肪链的岩藻糖衍生物，以增加疏水接触。相当通用的方法涉及顺序应用来自大肠杆菌的重组酶 L-岩藻糖 1-磷酸醛缩酶 (FucA) 和 L-岩藻糖酮醇异构酶 (FucI)。从适当的羟基醛前体和磷酸二羟基丙酮作为容易获得的组分开始，已制备出对映体纯的 L-岩藻糖类似物，总收率高达 30%。通过将烷（烯/炔）基格氏试剂加成到肉桂醛上，然后对苯乙烯片段进行受控臭氧分解，可以有效地制备不饱和 2-羟基醛。
A short enzymatic route for the synthesis ofL‐fucose analogs modified at the nonpolar terminus is reported. In particular, fucose derivatives bearing extended linear (1b) and branched (1e) saturated, or various unsaturated (1c,1d) aliphatic chains have been prepared, in order to increase hydrophobic contacts. The rather general approach involves a sequential application of the recombinant enzymesL‐fuculose 1‐phosphate aldolase (FucA) andL‐fucose ketol isomerase (FucI) fromE.coli. Enantiomerically pureL‐fucose analogs have been prepared in up to 30% overall yield starting from the appropriate hydroxyaldehyde precursors and dihydroxyacetone phosphate as readily available components. Unsaturated 2‐hydroxyaldehydes have been efficiently prepared by alk(en/yn)yl Grignard addition to cinnamaldehyde followed by controlled ozonolysis of the styrene fragment.