shikimate kinase | 9031-51-0

• 分子结构分类: 转移酶 - 转移含磷基团 - 以醇基作为受体的磷酸转移酶
• 英文名称: shikimate kinase
• 英文别名: shikimate kinase (phosphorylating)；shikimate kinase II；type II shikimate kinase (EC 2.7.1.71) from Escherichia coli
• CAS: 9031-51-0

反应信息

• 作为试剂：
  描述：

  4-benzoyloxy-2-cyclopentenone 在 shikimate kinase 、 potassium carbonate 三乙烯二胺 、 咪唑 、 盐酸 、 sodium tetrahydroborate 、 四氧化锇 、 NaOH buffer 、 cerium(III) chloride 、 deuterated triethanolamine*HCl 、 potassium carbonate 、 adenosine 5'-triphosphate disodium salt 、 magnesium chloride 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 418.5h， 生成 (+)-(E)-O-2-phospho-[2(R),3(S),4(R)]-trihydroxycyclopentylideneacetic acid
  参考文献：
  名称：

  Five-Membered Ring Analogues of Shikimic Acid

  摘要：

  Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer Limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogues of shikimic acid. Enzymatic studies showed that analogues 1-3 are indeed processed by shikimate kinase to give phosphates I-P, 2-P, and 3-P as five-membered ring analogues of shikimate-3-phosphate. In particular, analogue 1 is converted by the enzyme at a rate only 3.5-fold slower than that of the native substrate, while analogue 3 binds to shikimate kinase with an apparent K-m of 1.7 mM, compared to 0.14 mM for shikimate.

  DOI：

  10.1021/jo001121k