Article · Wikipedia archive · Last revised Jun 19, 2026

Neamine

Neamine is a degradation product of the aminoglycoside antibiotic neomycin. Several derivatives of neamine are active against susceptible and resistant Gram-positive and Gram-negative bacteria.

Last revised
Jun 19, 2026
Read time
≈ 1 min
Length
270 w
Citations
5
Source
Wikipedia ↗
Neamine
Clinical data
Other namesNeomycin A
Identifiers
  • (1R,2R,3S,4R,6S)-4,6-Diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H26N4O6
Molar mass322.362 g·mol−1
3D model (JSmol)
  • 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=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:345

2D representation of the chemical structure of Q27133569.
6'-Oxoparomamine
+
 
2D representation of the chemical structure of Q26995161.
L-Glutamic acid
 
 
 
Reversible left-right reaction arrow
 
 
 
2D representation of the chemical structure of Neamine.
Neamine
+
 
2D representation of the chemical structure of α-Ketoglutaric acid .
α-Ketoglutaric acid
Kanamycin A source ↗
References

References

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.