From Wikipedia, the free encyclopedia
Enduracididine
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Names
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IUPAC name
3-[(4R)-2-Imino-4-imidazolidinyl]-L-alanine
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Identifiers
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ChEBI
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ChemSpider
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KEGG
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UNII
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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
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C1[C@H](NC(=N)N1)C[C@@H](C(=O)O)N
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Properties
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C6H12N4O2
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Molar mass
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172.188 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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
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^ 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.
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^ 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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