Neamine

Neamine
Clinical data
Other names	Neomycin A
Identifiers
	IUPAC name (1R,2R,3S,4R,6S)-4,6-Diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside;
CAS Number	3947-65-7;
PubChem CID	72392;
DrugBank	DB04808;
ChemSpider	65325;
UNII	5981U00LY0;
CompTox Dashboard (EPA)	DTXSID7023358 ;
Chemical and physical data
Formula	C12H26N4O6
Molar mass	322.362 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O([C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N)[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2N)CN;
	InChI InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1; Key:SYJXFKPQNSDJLI-HKEUSBCWSA-N;

Neamine (neomycin A) is a degradation product of the aminoglycoside antibiotic neomycin.^[1] Several derivatives of neamine are active against susceptible and resistant Gram-positive and Gram-negative bacteria.^[2]

Biosynthesis

Neamine is a biosynthetic intermediate in the pathway which bacteria such as Streptomyces kanamyceticus use to make aminoglycoside antibiotics including lividomycin, neomycin and kanamycin. The immediate precursor is the aldehyde, 6'-oxoparomamine, which is acted on by the enzyme neamine transaminase:^[3]^[4]^[5]

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↑ Leach BE, Teeters CM (June 1951). "Neamine, an Antibacterial Degradation Product of Neomycin". Journal of the American Chemical Society. 73 (6): 2794–2797. doi:10.1021/ja01150a107.
↑ Zimmermann L, Bussière A, Ouberai M, Baussanne I, Jolivalt C, Mingeot-Leclercq MP, et al. (October 2013). "Tuning the antibacterial activity of amphiphilic neamine derivatives and comparison to paromamine homologues". Journal of Medicinal Chemistry. 56 (19): 7691–7705. doi:10.1021/jm401148j. PMID 24083676.
↑ Huang F, Spiteller D, Koorbanally NA, Li Y, Llewellyn NM, Spencer JB (February 2007). "Elaboration of neosamine rings in the biosynthesis of neomycin and butirosin". ChemBioChem. 8 (3): 283–8. doi:10.1002/cbic.200600371. PMID 17206729.
↑ Clausnitzer D, Piepersberg W, Wehmeier UF (September 2011). "The oxidoreductases LivQ and NeoQ are responsible for the different 6'-modifications in the aminoglycosides lividomycin and neomycin". Journal of Applied Microbiology. 111 (3): 642–51. doi:10.1111/j.1365-2672.2011.05082.x. PMID 21689223.
↑ Park JW, Park SR, Nepal KK, Han AR, Ban YH, Yoo YJ, et al. (October 2011). "Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation". Nature Chemical Biology. 7 (11): 843–52. doi:10.1038/nchembio.671. PMID 21983602.