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Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2.

ABSTRACT: 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.

SUBMITTER: Rajasekaran P

PROVIDER: S-EPMC7237068 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2.

Rajasekaran Parasuraman P Crich David D

Organic letters 20200428 10

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 de ...[more]

PMID: 32343899

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