Biosynthesis of the N-N-Bond-Containing Compound l-Alanosine.
Angew Chem Int Ed Engl
; 59(10): 3881-3885, 2020 03 02.
Article
em En
| MEDLINE
| ID: mdl-31823464
ABSTRACT
The formation of a N-N bond is a unique biochemical transformation, and nature employs diverse biosynthetic strategies to activate nitrogen for bond formation. Among molecules that contain a N-N bond, biosynthetic routes to diazeniumdiolates remain enigmatic. We here report the biosynthetic pathway for the diazeniumdiolate-containing amino acid l-alanosine. Our work reveals that the two nitrogen atoms in the diazeniumdiolate of l-alanosine arise from glutamic acid and aspartic acid, and we clarify the early steps of the biosynthetic pathway by using both inâ
vitro and inâ
vivo approaches. Our work demonstrates a peptidyl-carrier-protein-based mechanism for activation of the precursor l-diaminopropionate, and we also show that nitric oxide can participate in non-enzymatic diazeniumdiolate formation. Furthermore, we demonstrate that the gene alnA, which encodes a fusion protein with an N-terminal cupin domain and a C-terminal AraC-like DNA-binding domain, is required for alanosine biosynthesis.
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MEDLINE
Assunto principal:
Alanina
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article