Bekanamycin

Bekanamycin
Names
	IUPAC name (2S,3R,4S,5S,6R)-4-amino-2-{[(2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol;
Clinical data
WHO AWaRe
External links
AHFS/Drugs.com	International Drug Names
Legal
Legal status	In general: ℞ (Prescription only);
Chemical and physical data
Formula	C18H37N5O10
Molar mass	483.519 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N;
	InChI InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1 ; Key:SKKLOUVUUNMCJE-FQSMHNGLSA-N ;

Bekanamycin (INN; kanamycin B) is an aminoglycoside antibiotic.^[1]^[2] Per an article in Nature 2011, it was discovered that parallel pathways of kanamycin biosynthesis occurs^[3] though other article(s) have indicated a different proposal.^[4]

(Proposed) linear kanamycin biosynthetic pathways.^[4]

References

↑ Morales MA, Castrillon JL, Hernandez DA (1993). "Effects of bekanamycin and dibekacin on the electrical activity of cardiac pacemaker cells". Archives of Medical Research. 24 (4): 339–45. PMID 8118157.
↑ PubChem. "Bekanamycin". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2023-06-03. Retrieved 2023-07-04.
↑ Park, Je Won; Park, Sung Ryeol; Nepal, Keshav Kumar; Han, Ah Reum; Ban, Yeon Hee; Yoo, Young Ji; Kim, Eun Ji; Kim, Eui Min; Kim, Dooil; Sohng, Jae Kyung; Yoon, Yeo Joon (9 October 2011). "Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation". Nature Chemical Biology. 7 (11): 843–852. doi:10.1038/nchembio.671. ISSN 1552-4469. Archived from the original on 12 February 2023. Retrieved 23 August 2023.
↑ ^4.0 ^4.1 Gao, W; Wu, Z; Sun, J; Ni, X; Xia, H (2017). "Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering". PloS one. 12 (7): e0181971. doi:10.1371/journal.pone.0181971. PMID 28753625. Retrieved 23 August 2023.. These results clarified that kanamycin biosynthesis does not proceed through the parallel pathway and that synthesis of kanamycin A from kanamycin B is catalyzed by KanJ and KanK in S. kanamyceticus

External links

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[1] Morales MA, Castrillon JL, Hernandez DA (1993). "Effects of bekanamycin and dibekacin on the electrical activity of cardiac pacemaker cells". Archives of Medical Research. 24 (4): 339–45. PMID 8118157.

[2] PubChem. "Bekanamycin". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2023-06-03. Retrieved 2023-07-04.

[3] Park, Je Won; Park, Sung Ryeol; Nepal, Keshav Kumar; Han, Ah Reum; Ban, Yeon Hee; Yoo, Young Ji; Kim, Eun Ji; Kim, Eui Min; Kim, Dooil; Sohng, Jae Kyung; Yoon, Yeo Joon (9 October 2011). "Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation". Nature Chemical Biology. 7 (11): 843–852. doi:10.1038/nchembio.671. ISSN 1552-4469. Archived from the original on 12 February 2023. Retrieved 23 August 2023.

[re-4] 4.0 ^4.1 Gao, W; Wu, Z; Sun, J; Ni, X; Xia, H (2017). "Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering". PloS one. 12 (7): e0181971. doi:10.1371/journal.pone.0181971. PMID 28753625. Retrieved 23 August 2023.. These results clarified that kanamycin biosynthesis does not proceed through the parallel pathway and that synthesis of kanamycin A from kanamycin B is catalyzed by KanJ and KanK in S. kanamyceticus

[1]

[2]

[3]

[4]

Names

IUPAC name (2S,3R,4S,5S,6R)-4-amino-2-{[(2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol
Clinical data
WHO AWaRe
External links
AHFS/Drugs.com	International Drug Names
Legal
Legal status	In general: ℞ (Prescription only)
Chemical and physical data
Formula	C₁₈H₃₇N₅O₁₀
Molar mass	483.519 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
InChI InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1^Y Key:SKKLOUVUUNMCJE-FQSMHNGLSA-N^Y

Bekanamycin

References

External links

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