醛缩酶 RhaD 合成 D-山梨糖和 D-阿洛酮糖的酶法：受体构型对酶立体选择性的影响。
Enzymatic synthesis of D-sorbose and D-psicose with aldolase RhaD: effect of acceptor configuration on enzyme stereoselectivity.
机构信息
Department of Chemistry, Georgia State University, Atlanta, GA 30302, USA.
出版信息
Bioorg Med Chem Lett. 2011 Dec 1;21(23):7081-4. doi: 10.1016/j.bmcl.2011.09.087. Epub 2011 Sep 29.
Abstract
It was previously reported that DHAP-dependent aldolase RhaD selectively chooses L-glyceraldehyde from racemic glyceraldehyde to produce l-fructose exclusively. Contrastingly, we discovered that D-glyceraldehyde is also tolerated as an acceptor and the stereoselectivity of the enzyme is lost in the corresponding aldol addition. Furthermore, we applied this property to efficiently synthesize two rare sugars D-sorbose and D-psicose.
摘要
先前有报道称，DHAP 依赖性醛缩酶 RhaD 能从外消旋甘油醛中选择性地选择 L-甘油醛，从而专一性地生成 l-果糖。相比之下，我们发现 D-甘油醛也可被接受，且酶的立体选择性在相应的醛醇加成中丧失。此外，我们利用这一性质高效合成了两种稀有糖 D-山梨糖和 D-阿洛酮糖。
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2
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3
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Appl Microbiol Biotechnol. 2006 Jul;71(3):253-64. doi: 10.1007/s00253-006-0422-6. Epub 2006 Apr 14.
9
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10
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