Tyrosine O-prenyltransferases TyrPT and SirD displaying similar behavior toward unnatural alkyl or benzyl diphosphate as their natural prenyl donor dimethylallyl diphosphate

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• 作者：Huili Yu ; Mike Liebhold ; Xiulan Xie ; Shu-Ming Li
• 关键词：DMATS superfamily ; Unnatural alkyl donors ; Tyrosine and derivatives ; Enzyme catalysis
• 刊名：Applied Microbiology and Biotechnology
• 出版年：2015
• 出版时间：September 2015
• 年：2015
• 卷：99
• 期：17
• 页码：7115-7124
• 全文大小：1,520 KB
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• 作者单位：Huili Yu (1)
  Mike Liebhold (1)
  Xiulan Xie (2)
  Shu-Ming Li (1)
  
  1. Institut f眉r Pharmazeutische Biologie und Biotechnologie, Philipps-Universit盲t Marburg, Deutschhausstrasse 17A, 35037, Marburg, Germany
  2. Fachbereich Chemie, Philipps-Universit盲t Marburg, Hans-Meerwein-Stra脽e 4, 35032, Marburg, Germany
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Biotechnology
  Microbiology
  Microbial Genetics and Genomics
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1432-0614

文摘

Prenyltransferases of the dimethylallyltryptophan synthase (DMATS) superfamily are involved in the biosynthesis of secondary metabolites and contribute as modification enzymes significantly to structural diversity of natural products. They show usually broad specificity toward their aromatic substrates with regiospecific prenylations on aromatic rings. However, most members of this superfamily exhibit a high specificity toward their prenyl donors and usually accept exclusively dimethylallyl diphosphate (DMAPP). Recently, several indole prenyltransferases from this family were also demonstrated to accept unnatural DMAPP analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring. Partial or complete shift of the substitution position was observed for these enzymes. In this study, we report the acceptance of these DMAPP analogs by two tyrosine O-prenyltransferases TyrPT from Aspergillus niger and SirD from Leptosphaeria maculans for alkylation or benzylation of tyrosine and derivatives. NMR and mass spectrometry (MS) analyses of nine isolated enzyme products confirmed the regiospecific O- or N-alkylation or benzylation at position C-4 of the aromatic ring, which is the same prenylation position of these enzymes in the presence of DMAPP.