NTR: N-methyl-L-valine

[althonos]

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.)

[ricardblum]

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 :

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