Enduracididine

Enduracididine
Names
	IUPAC name 3-[(4R)-2-Imino-4-imidazolidinyl]-L-alanine
Identifiers
CAS Number	21209-39-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:73969;
ChemSpider	24775830;
KEGG	C20602;
PubChem CID	15284838;
UNII	V9U5NAX243 ;
CompTox Dashboard (EPA)	DTXSID801032117 ;
	InChI 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;
	SMILES C1[C@H](NC(=N)N1)C[C@@H](C(=O)O)N;
Properties
Chemical formula	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

^ 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.
^ 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.

[Atkinson2016-1] 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.

[Ling2015-2] 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.

[1]

[2]