Enduracididine
Names
IUPAC name
3-[(4R)-2-Imino-4-imidazolidinyl]-L-alanine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C6H12N4O2/c7-4(5(11)12)1-3-2-9-6(8)10-3/h3-4H,1-2,7H2,(H,11,12)(H3,8,9,10)/t3-,4+/m1/s1
    Key: VFXRPXBQCNHQRQ-DMTCNVIQSA-N
  • InChI=1/C6H12N4O2/c7-4(5(11)12)1-3-2-9-6(8)10-3/h3-4H,1-2,7H2,(H,11,12)(H3,8,9,10)/t3-,4+/m1/s1
    Key: VFXRPXBQCNHQRQ-DMTCNVIQBA
  • C1[C@H](NC(=N)N1)C[C@@H](C(=O)O)N
Properties
C6H12N4O2
Molar mass 172.188 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Enduracididine is a non-proteinogenic α-amino acid that is a cyclic analogue of arginine.[1] It is not genetically encoded into peptide sequences, but rather is generated as a posttranslational modification.

Biological roles

Enduracididine occurs rarely in nature, appearing principally in peptide antibiotics such as the antibacterial compounds enramycin and teixobactin.[2]

References

  1. ↑ Atkinson, DJ; Naysmith, BJ; Furkert, DP; Brimble, MA (7 November 2016). "Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis". Beilstein J Org Chem. 12: 2325–2342. doi:10.3762/bjoc.12.226. PMC 5238550. PMID 28144300.
  2. ↑ Ling, LL; Schneider, T; Peoples, AJ; Spoering, AL; Engels, I; Conlon, BP; Mueller, A; Schäberle, TF; Hughes, DE; Epstein, S; Jones, M; Lazarides, L; Steadman, VA; Cohen, DR; Felix, CR; Fetterman, KA; Millett, WP; Nitti, AG; Zullo, AM; Chen, C; Lewis, K (22 January 2015). "A new antibiotic kills pathogens without detectable resistance". Nature. 517 (7535): 455–9. doi:10.1038/nature14098. PMC 7414797. PMID 25561178.
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