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Study · In vitro (cells) · 2018

1 result

Structural modification of the tripeptide KPV by reductive "glycoalkylation" of the lysine residue.

Songok AC, Panta P, Doerrler WT, Macnaughtan MA, Taylor CM

PloS one28 Jun 2018Cited by 5 (Europe PMC)

PMID29953505 (opens in a new tab)PMCIDPMC6023233 (opens in a new tab)DOI10.1371/journal.pone.0199686 (opens in a new tab)PepBankPUB-29953505
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Summary

Peptides that exhibit enzymatic or hormonal activities are regulatory factors and desirable therapeutic drugs because of their high target specificity and minimal side effects. Unfortunately, these drugs are susceptible to enzymatic degradation, leading to their rapid elimination and thereby demanding frequent dosage. Structurally modified forms of some peptide drugs have shown enhanced pharmacokinetics, improving their oral bioavailability. Here, we discuss a novel glycomimetic approach to modify lysine residues in peptides. In a model system, the ε-amine of Ts-Lys-OMe was reductively alkylated with a glucose derivative to afford a dihydroxylated piperidine in place of the amine. A similar modification was applied to H-KPV-NH2, a tripeptide derived from the α-melanocyte stimulating hormone (α-MSH) reported to have antimicrobial and anti-inflammatory properties. Antimicrobial assays, under a variety of conditions, showed no activity for Ac-KPV-NH2 or the α- or ε-glycoalkylated analogs. Glycoalkylated peptides did, however, show stability toward proteolytic enzymes.
CC BYText from Europe PMC. Highlighted sentences are the source of results.

Results from this study1

1 result from studies that gave the peptide. No result from this study comes from people.

  1. 01LabIn vitro (cells)Activity measurement

    In antimicrobial assays under a variety of conditions, Ac-KPV-NH2 showed no activity.

    In plain wordsIn lab tests, the KPV form Ac-KPV-NH2 showed no antimicrobial activity.

    Peptide
    KPV
    Outcome
    No significant changeAntimicrobial activity of Ac-KPV-NH2
    Study

    n: not reported in source

    Outcome group
    Infection and antimicrobial activity · Infection
    Studied dose
    Dose not stated

    Source sentences

    Summary
    Antimicrobial assays, under a variety of conditions, showed no activity for Ac-KPV-NH2 or the α- or ε-glycoalkylated analogs.

AI wrote and checked these results. AI can make mistakes, so check important results against the source.

Version history

PepBank keeps every version of the data on this study. Status changes from Retraction Watch, Europe PMC and Crossref are listed with their source.

  1. Version 3Current

    9 Oct 2026, 18:17 UTC

    Study results updated

  2. Version 2

    9 Oct 2026, 03:03 UTC

    Study data updated · source update from Europe PMC

  3. Version 1

    9 Oct 2026, 02:56 UTC

    First added · source update from Europe PMC

Subjects

Terms as the source lists them.

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