ricardblum
commented
2 years ago Hi Martin and Eric,
Information on N-methyl-valine is listed below. Please feel free to complete/update it.
Many thanks.
Sylvie.
Modified and unusual Amino Acid
A non-proteinogenic amino acid N-Methyl-L-valine Abbreviation: MeVal 3-methyl-2-(methylamino)butanoic acid C_6 H_13 NO_2 Average Mw: 131.1729 Monoisotopic Mw131.094628665
Low level of methylated valine was detected at trace level in a soil sample using gas chromatography coupled with mass spectrometry (GC/ MS) (DOI:10.2136/sssaj2000.642583x)
Present in organic compounds
- Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase (PMID: 12203574)
- Inhibition of beta-amyloid(40) fibrillogenesis and disassembly of beta-amyloid(40) fibrils by short beta-amyloid congeners containing N-methyl amino acids at alternate residues (PMID: 11444969)**
Biosynthesis of methylvaline
The B12-dependent radical S-adenosylmethionine (rSAM) enzyme PoyC catalyzes peptide Cβ-methylation. PoyC catalyzes the formation of S-adenosylhomocysteine and 5'-deoxyadenosine and the transfer of a methyl group to l-valine residue Reference: the B 12-Radical SAM Enzyme PoyC Catalyzes Valine C β-Methylation during Polytheonamide Biosynthesis (PMID: 27934015)
Analysis
ESI-MS/MS analysis of protonated N-methyl amino acids and their immonium ions including N-methylvaline (PMID: 31412140)
Found in the following databases
- Chemical Entities of Biological Interest(ChEBI) https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44212 - PubChem CID 4378 N-methylvaline https://pubchem.ncbi.nlm.nih.gov/compound/N-Methylvaline - The Human Metabolome Database https://hmdb.ca/metabolites/HMDB0061716__ - MetaCyc, a curated database of experimentally elucidated metabolic pathways from all domains of life https://biocyc.org/compound?orgid=META&id=CPD0-1059# https://biocyc.org/compound?orgid=META&id=CPD0-1059
Le 25/02/2022 à 06:40, Eric Deutsch a écrit :
Assigned #65 https://github.com/HUPO-PSI/psi-mod-CV/issues/65 to @ricardblum https://github.com/ricardblum.
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Hi!
There's no term for N-methylated valine residues currently; this would be useful to describe some peptides such as omphalotin A, which contains MeVal residues:
(from Thern B, Rudolph J, Jung G. Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase. Angew Chem Int Ed Engl. 2002 Jul 2;41(13):2307-9. doi: 10.1002/1521-3773(20020703)41:13<2307::AID-ANIE2307>3.0.CO;2-Y. PMID: 12203574.)