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Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase

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논문

Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase

학술지

European journal of organic chemistry

저자명

Yu, Jinhai; Li, Jing; Gao, Xia; Zeng, Shuiyun; Zhang, Hongjuan; Liu, Junzhong; Jiao, Qingcai

초록

<P>L&#8208;Ser is often used to synthesize some significant <SMALL>l</SMALL>&#8208;noncanonical &alpha;&#8208;amino acids(<SMALL>l</SMALL>&#8208;ncAAs), which are the prevalent intermediates and precursors for functional synthetic compounds. In this study, threonine aldolase from <I>Escherichia coli</I> k&#8208;12 MG1655 has been used to synthesize <SMALL>l</SMALL>&#8208;Ser. In contrast to the maximum catalytic capacity (20 g/L) for <SMALL>l</SMALL>&#8208;threonine aldolase(LTA), <SMALL>d</SMALL>&#8208;Ser was synthesized with high yield (240 g/L) from cheap Gly and paraformaldehyde using <SMALL>d</SMALL>&#8208;threonine aldolase (DTA) from <I>Arthrobacter sp</I> ATCC. In order to fully utilize <SMALL>d</SMALL>&#8208;Ser and expand the resource of <SMALL>l</SMALL>&#8208;Ser, a dynamic kinetic resolution system was constructed to convert <SMALL>d</SMALL>/<SMALL>dl</SMALL>&#8208;Ser to <SMALL>l</SMALL>&#8208;Ser through combining alanine racemase (Alr) from <I>Bacillus subtilis</I> with <SMALL>l</SMALL>&#8208;tryptophan synthase (TrpS) from <I>Escherichia coli</I> k&#8208;12 MG1655, and <SMALL>l</SMALL>&#8208;ncAAs including <SMALL>l</SMALL>&#8208;Trp and <SMALL>l</SMALL>&#8208;Cys derivatives were synthesized with excellent enantioselectivity and in high yields. The results indicated <SMALL>l</SMALL>&#8208;ncAAs could be efficiently synthesized from <SMALL>d</SMALL>&#8208;Ser using this original and green dynamic kinetic resolution system, and the reliable <SMALL>l</SMALL>&#8208;Ser resource has been established from simple and achiral substrates.</P>

발행연도

2019

ISSN

1434-193x

ISSN

1099-0690

2019

39

페이지

pp.6618-6625

주제어

Alanine Racemase; Dynamic Kinetic Resolution; d&#x2010; Threonine Aldolase; l&#x2010; Noncanonical Amino Acids; Tryptophan Synthase;

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1 2023-12-11
2 2023-12-11
3 2023-12-11

논문; 2019-10-14

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