Enduracididine

Enduracididine
Names
	IUPAC name 3-[(4R)-2-Imino-4-imidazolidinyl]-L-alanine
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	24775830;
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 an α-amino acid that is non-proteinogenic. It corresponds to alanine with 2-imino-4-imidazolidinyl group in place of a methyl hydrogen.

Biological roles

Enduracididine is not genetically encoded in protein sequences, but rather is generated as a posttranslational modification. For example, enduracididine is found in the antibacterial compound teixobactin.^[1]

References

^ 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. PMID 25561178.

[Ling2015-1] 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. PMID 25561178.

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