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Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids.

ABSTRACT: The glycosyltransferase OleD variant as a catalyst for the glycosylation of four pairs of epimers of cardiotonic steroids (CTS) are assessed. The results of this study demonstrated that the OleD-catalyze glycosylation of CTS is significantly influenced by the configuration at C-3 and the A/B fusion mode. 3β-OH and A/B ring cis fusion are favoured by OleD (ASP). An epoxide ring at C-14 and C-15 further increases the bioconversion rate; while an acetyl group at C-16 and lactone ring type at C-17 did not influence the biotransformation. A high conversion rate corresponded to a low K _m value. A molecular docking simulation showed that filling of hydrophobic pocket II and interaction with residue Tyr115 may play an important role in the glycosylation reactions catalyzed by OleD glycosyltransferases. Furthermore, the glycosylation products showed a stronger inhibitory activity for Na⁺, K⁺-ATPase than the corresponding aglycones. This study provides the first stereoselective properties for OleD (ASP) catalyzed glycosylation.

SUBMITTER: Zhu XL

PROVIDER: S-EPMC9078122 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids.

Zhu Xue-Lin XL Wen Chao C Ye Qing-Mei QM Xu Wei W Zou Deng-Lang DL Liang Guang-Ping GP Zhang Fan F Chen Wan-Na WN Jiang Ren-Wang RW

RSC advances 20180130 10

The glycosyltransferase OleD variant as a catalyst for the glycosylation of four pairs of epimers of cardiotonic steroids (CTS) are assessed. The results of this study demonstrated that the OleD-catalyze glycosylation of CTS is significantly influenced by the configuration at C-3 and the A/B fusion mode. 3β-OH and A/B ring <i>cis</i> fusion are favoured by OleD (ASP). An epoxide ring at C-14 and C-15 further increases the bioconversion rate; while an acetyl group at C-16 and lactone ring type at ...[more]

PMID: 35542447

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Dataset Information

Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids.

Publications

Probing the stereoselectivity of OleD-catalyzed glycosylation of cardiotonic steroids.

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