Pseudopeptides with a centrally positioned alkene-based disulphide bridge mimetic stimulate kallikrein-related peptidase 3 activity

• Pseudopeptides based on the kallikrein-related peptidase 3 (KLK3) activating bicyclic peptide “C-4” comprising hydrocarbon-based disulphide bridge mimetics have been synthesized. After investigating different synthetic approaches, the pseudopeptides were successfully cyclized from two L-allylglycine side chains via an alkene ring-closing metathesis reaction during the peptide synthesis. The alkene-linker was formed in a 1 : 1 E/Z isomer ratio. The resulting pseudopeptides were almost as potent as the parent peptide, increasing the activity of KLK3 over four-fold at 200 μg ml−1 (130–140 μM) concentrations.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Nyckelord

prostate-specific antigen

ring-closing metathesis

antiangiogenic

activity

binding

analogs

cancer

klk3

RMANYnullABRAHAMSSON

PAABRAHAMSSON

PALILJA

HLILJA

HFALKMER

SFALKMER

arlstrom

KCarlstrom

KTribukait

BTribukait

BPousette

APousette

A20006160CLINICAL CANCER

GANIC CHEMISTRYnullStenman

UHStenman

UHLeinonen

JLeinonen

JZhang

WMZhang

WMFinne

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