36889-17-5Relevant articles and documents
Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2
Crich, David,Rajasekaran, Parasuraman
supporting information, p. 3850 - 3854 (2020/06/04)
The clinical aminoglycoside antibiotic gentamicin is a mixture of several difficult-to-separate major and minor components. The relative inaccessibility of the minor components in particular complicates efforts to separate antibacterial activity from nephro- and/or ototoxicity and to clarify the origin of the potentially therapeutically important read-through activity. With a view to facilitating such studies, the synthesis of a fully and selectively protected garamine-based acceptor has been developed from readily available sisomicin. Glycosylation of this acceptor with a 6-azido-6,7-dideoxy-d-glycero-d-glucoheptopyranosyl donor affords gentamicin B1 after deprotection, whereas employment of a 2-azido-2-deoxy-d-glucopyranosyl donor under N,N-dimethylformamide-directed glycosylation conditions affords gentamicin X2 after deprotection.
Bausteine von Oligosacchariden, XXI. Synthesen von Gentamicin X2 und am C-4' und C-3' modifizierter Gentamicine
Paulsen, Hans,Schroeder, Bernd,Boettcher, Henning,Hohlweg, Rolf
, p. 322 - 332 (2007/10/02)
The garamine derivative 18 can be coupled with the β-chloride 15 of 2-azido-2-deoxy-D-glucose to 20 from which, by deblocking procedure, gentamicin X2 (23) is available.In the same manner the 4'-amino- and 4'-chloro compound 24 and 25, resp., can be obtained.Coupling of 26 with 19 gives the product 27 from which the derivative 28 of gentamicin, modified at C-3', is prepared.
