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Efficient Synthesis of 12-Oxochenodeoxycholic Acid Using a 12α-Hydroxysteroid Dehydrogenase from Rhodococcus ruber

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    • 바이오플라스틱
      1. 플라스틱
    • 바이오정밀화학
      1. 기타
    • 화장품용 기능성소재
      1. 기능성
      2. 계면활성제⁄증점제
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      1. 치료제
      2. 식품첨가제
논문

Efficient Synthesis of 12-Oxochenodeoxycholic Acid Using a 12α-Hydroxysteroid Dehydrogenase from Rhodococcus ruber

학술지

Advanced synthesis & catalysis

저자명

Shi, Shou‐ Cheng; You, Zhi‐ Neng; Zhou, Ke; Chen, Qi; Pan, Jiang; Qian, Xiao‐ Long; Xu, Jian‐ He; Li, Chun‐ Xiu

초록

<P><B>Abstract</B></P><P>12&alpha;&#8208;Hydroxysteroid dehydrogenase (12&alpha;&#8208;HSDH) has the potential to convert cheap and readily available cholic acid (CA) to 12&#8208;oxochenodeoxycholic acid (12&#8208;oxo&#8208;CDCA), a key precursor for chemoenzymatic synthesis of the therapeutic bile acid ursodeoxycholic acid (UDCA). In this work, a native nicotinamide adenine dinucleotide (NAD<SUP>+</SUP>)&#8208;dependent 12&alpha;&#8208;hydroxysteroid dehydrogenase (<I>Rr</I>12&alpha;&#8208;HSDH) from <I>Rhodococcus ruber</I> was identified using a structure&#8208;guided genome mining (SSGM) approach, which is based on the structure of cofactor pocket and the conserved nicotinamide cofactor binding motif alignment. <I>Rr</I>12&alpha;&#8208;HSDH was heterologously overexpressed in <I>Escherichia coli</I> BL21 (DE3), purified and characterized. The purified <I>Rr</I>12&alpha;&#8208;HSDH showed a high oxidative activity of 290 U mg<SUP>&minus;1</SUP><SUB>protein</SUB> toward CA, with a catalytic efficiency (<I>k</I><SUB>cat</SUB>/<I>K</I><SUB>M</SUB>) of 5.10&times;10<SUP>3</SUP> mM<SUP>&minus;1</SUP> s<SUP>&minus;1</SUP>. In a preparative biotransformation (100 mL), CA (200 mM, 80 g L<SUP>&minus;1</SUP>) was efficiently converted to 12&#8208;oxo&#8208;CDCA in 1 h, with a 85% isolated yield and a space&#8208;time yield (STY) of up to 1632 g L<SUP>&minus;1</SUP> d<SUP>&minus;1</SUP>. Furthermore, <I>Rr</I>12&alpha;&#8208;HSDH was shown to be able to catalyze the oxidation of other 12&alpha;&#8208;hydroxysteroids at high substrate loads (up to 200 mM), giving the corresponding 12&#8208;oxo&#8208;hydroxysteroids in 71%&ndash;85% yields, indicating the great potential of <I>Rr</I>12&alpha;&#8208;HSDH as a promising biocatalyst for the synthesis of various therapeutic bile acids.</P>

발행연도

2019

ISSN

1615-4150

ISSN

1615-4169

361

20

페이지

pp.4661-4668

주제어

biocatalysis; 12α-hydroxysteroid dehydrogenase; NAD+-dependence; structure-guided genome mining; 12-oxochenodeoxycholic acid

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논문; 2019-12-31

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