Azirinomycin

Azirinomycin
Names
	IUPAC name 3-Methyl-2H-azirine-2-carboxylic acid
Identifiers
CAS Number	31772-89-1 [ EPA ];
3D model (JSmol)	Interactive image ;
ChemSpider	33047 ;
PubChem CID	35931 ;
CompTox Dashboard (EPA)	DTXSID10953710 ;
	InChI InChI=1S/C4H5NO2/c1-2-3(5-2)4(6)7/h3H,1H3,(H,6,7) Key: NHCHAEIJXKFNRU-UHFFFAOYSA-N;
	SMILES CC1=NC1C(=O)O;
Properties
Chemical formula	C4H5NO2
Molar mass	99.089 g·mol−1
Related compounds
Related compounds	Azirine ; Motualevic acid F
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated June 08, 2025

Azirinomycin is an antibiotic azirine derivative with the molecular formula C₄H₅NO₂ which is produced by the bacterium Streptomyces aureus .^[1]^[2]^[3] Azirinomycin was first isolated in 1971.^[4] Azirinomycin is toxic and therefore it cannot not be used in human medicine.^[4]

References

1 2 "3-Methyl-2H-azirine-2-carboxylic acid". pubchem.ncbi.nlm.nih.gov.
↑ Communications, EBCONT. "Azirinomycin". roempp.thieme.de.
↑ Stapley, Edward O.; Hendlin, David; Jackson, Marion; Miller, A. Kathrine; Hernandez, Sebastian; Mata, Justo M. (25 January 1971). "Azirinomycin. I". The Journal of Antibiotics. 24 (1): 42–47. doi: 10.7164/antibiotics.24.42 . ISSN 0021-8820.
1 2 Diana, Patrizia; Cirrincione, Girolamo (30 January 2015). Biosynthesis of Heterocycles: From Isolation to Gene Cluster. John Wiley & Sons. p. 101. ISBN 978-1-118-96042-4.

Miller, TW; Tristram, EW; Wolf, FJ (January 1971). "Azirinomycin. II. Isolation and chemical characterization as 3-methyl-2(2H) azirinecarboxylic acid". The Journal of Antibiotics. 24 (1): 48–50. doi: 10.7164/antibiotics.24.48 . PMID 5541332.
Stapley, EO; Hendlin, D; Jackson, M; Miller, AK; Hernandez, S; Mata, JM (January 1971). "Azirinomycin. I. Microbial production and biological characteristics". The Journal of Antibiotics. 24 (1): 42–7. doi: 10.7164/antibiotics.24.42 . PMID 5541331.
Williams, R. M. (22 October 2013). Synthesis of Optically Active Alpha-Amino Acids. Elsevier. p. 126. ISBN 978-1-4832-9295-3.
Carreira, Erick M. (14 May 2014). Science of Synthesis Knowledge Updates 2011 Vol. 3. Georg Thieme Verlag. p. 137. ISBN 978-3-13-178751-4.

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[Azirinomycin-1] 1 2 "3-Methyl-2H-azirine-2-carboxylic acid". pubchem.ncbi.nlm.nih.gov.

[2] Communications, EBCONT. "Azirinomycin". roempp.thieme.de.

[3] Stapley, Edward O.; Hendlin, David; Jackson, Marion; Miller, A. Kathrine; Hernandez, Sebastian; Mata, Justo M. (25 January 1971). "Azirinomycin. I". The Journal of Antibiotics. 24 (1): 42–47. doi: 10.7164/antibiotics.24.42 . ISSN 0021-8820.

[Azirinomycin2-4] 1 2 Diana, Patrizia; Cirrincione, Girolamo (30 January 2015). Biosynthesis of Heterocycles: From Isolation to Gene Cluster. John Wiley & Sons. p. 101. ISBN 978-1-118-96042-4.

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Names

IUPAC name 3-Methyl-2H-azirine-2-carboxylic acid^[1]
Identifiers
CAS Number	31772-89-1 ^{N[ EPA ]}
3D model (JSmol)	Interactive image
ChemSpider	33047
PubChem CID	35931
CompTox Dashboard (EPA)	DTXSID10953710
InChI InChI=1S/C4H5NO2/c1-2-3(5-2)4(6)7/h3H,1H3,(H,6,7) Key: NHCHAEIJXKFNRU-UHFFFAOYSA-N
SMILES CC1=NC1C(=O)O
Properties
Chemical formula	C₄H₅NO₂
Molar mass	99.089 g·mol⁻¹
Related compounds
Related compounds	Azirine Motualevic acid F
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Azirinomycin

References

Further reading