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Biological matching of chemical reactivity: pairing indole nucleophilicity with electrophilic isoprenoids.

Abstract：

:The indole side chain of tryptophan has latent nucleophilic reactivity at both N1 and all six (nonbridgehead) carbons, which is not generally manifested in post-translational reactions of proteins. On the other hand, all seven positions can be prenylated by the primary metabolite Δ(2)-isopentenyl diphosphate by dimethyallyl transferase (DMATs) family members as initial steps in biosynthetic pathways to bioactive fungal alkaloids including ergots and tremorgens. These are formulated as regioselective capture of isopentenyl allylic cationic transition states by the indole side chain as a nucleophile. The balance of regiospecificity and promiscuity among these indole prenyltransferases continues to raise questions about possible Cope and azaCope rearrangements of nascent products. In addition to these two electron reaction manifolds, there is evidence for one electron reaction manifolds in indole ring biosynthetic functionalization.

journal_name

ACS Chem Biol

journal_title

ACS chemical biology

authors

Walsh CT

doi

10.1021/cb500695k

subject

Has Abstract

pub_date

2014-12-19 00:00:00

pages

2718-28

issue

12

eissn

1554-8929

issn

1554-8937

journal_volume

9

pub_type

杂志文章,评审

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