Piperazic acid-containing natural products: structures and biosynthesis.

Abstract:

:Covering: up to the end of 2018 Piperazic acid is a cyclic hydrazine and a non-proteinogenic amino acid found in diverse non-ribosomal peptide (NRP) and hybrid NRP-polyketide (PK) structures. Piperazic acid was first identified as a residue in the monamycins in 1959. Since then, the piperazic acid residue has been found in >30 families of natural products, representing >140 compounds. Many of these compounds have potent biological activity, ranging from anti-malarial to anti-apoptotic to anti-bacterial activity, although high toxicity often accompanies this potent biological activity. Recently, we identified a piperazate synthase, responsible for N-N bond formation to give piperazic acid. Here, we review piperazic acid-containing natural products discovered from 1959 to 2018, with an emphasis on the biosynthetic routes to these natural products.

journal_name

Nat Prod Rep

journal_title

Natural product reports

authors

Morgan KD,Andersen RJ,Ryan KS

doi

10.1039/c8np00076j

subject

Has Abstract

pub_date

2019-12-11 00:00:00

pages

1628-1653

issue

12

eissn

0265-0568

issn

1460-4752

journal_volume

36

pub_type

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