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The Role of a Nonribosomal Peptide Synthetase in L-Lysine Lactamization During Capuramycin Biosynthesis

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논문

The Role of a Nonribosomal Peptide Synthetase in L-Lysine Lactamization During Capuramycin Biosynthesis

학술지

Chembiochem : a European journal of chemical biology

저자명

Liu, Xiaodong; Jin, Yuanyuan; Cui, Zheng; Nonaka, Koichi; Baba, Satoshi; Funabashi, Masanori; Yang, Zhaoyong; Van Lanen, Steven G.

초록

<P><B>Abstract</B></P><P>Capuramycins are one of several known classes of natural products that contain an <SMALL>l</SMALL>&#8208;Lys&#8208;derived <SMALL>l</SMALL>&#8208;&alpha;&#8208;amino&#8208;&#603;&#8208;caprolactam (<SMALL>l</SMALL>&#8208;ACL) unit. The &alpha;&#8208;amino group of <SMALL>l</SMALL>&#8208;ACL in a capuramycin is linked to an unsaturated hexuronic acid component through an amide bond that was previously shown to originate by an ATP&#8208;independent enzymatic route. With the aid of a combined in vivo and in vitro approach, a predicted tridomain nonribosomal peptide synthetase CapU is functionally characterized here as the ATP&#8208;dependent amide&#8208;bond&#8208;forming catalyst responsible for the biosynthesis of the remaining amide bond present in <SMALL>l</SMALL>&#8208;ACL. The results are consistent with the adenylation domain of CapU as the essential catalytic component for <SMALL>l</SMALL>&#8208;Lys activation and thioesterification of the adjacent thiolation domain. However, in contrast to expectations, lactamization does not require any additional domains or proteins and is likely a nonenzymatic event. The results set the stage for examining whether a similar NRPS&#8208;mediated mechanism is employed in the biosynthesis of other <SMALL>l</SMALL>&#8208;ACL&#8208;containing natural products and, just as intriguingly, how spontaneous lactamization is avoided in the numerous NRPS&#8208;derived peptides that contain an unmodified <SMALL>l</SMALL>&#8208;Lys residue.</P>

발행연도

2016

ISSN

1439-4227

ISSN

1439-7633

17

9

페이지

pp.804-810

주제어

antibiotics; biosynthesis; natural products; nonribosomal peptides; nucleosides

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1 2023-12-11

논문; 2016-12-31

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