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Glycosylated PROLI/NO derivatives as nitric oxide prodrugs.

ABSTRACT: GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

SUBMITTER: Nandurdikar RS

PROVIDER: S-EPMC2808138 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Glycosylated PROLI/NO derivatives as nitric oxide prodrugs.

Nandurdikar Rahul S RS Maciag Anna E AE Hong Sam Y SY Chakrapani Harinath H Citro Michael L ML Keefer Larry K LK Saavedra Joseph E JE

Organic letters 20100101 1

GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO. ...[more]

PMID: 19954198

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