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Title of Journal: Amino Acids

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Abbravation: Amino Acids

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Springer Vienna

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DOI

10.1007/s11661-007-9424-y

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1438-2199

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Direct onestep labeling of cysteine residues on p

Authors: Joshua Chin Matthew Vesnaver Vadim BernardGauthier Erin SauckeLacelle Björn Wängler Carmen Wängler Ralf Schirrmacher
Publish Date: 2013/08/07
Volume: 45, Issue: 5, Pages: 1097-1108
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Abstract

Radiolabeled peptides have emerged as an attractive platform for the diagnostic and therapeutic oncology However the 11Cradiolabeling of peptides for positron emission tomography PET has been poorly explored owing to the relatively short halflife of carbon11 t 1/2 = 203 min and timeconsuming multistep radiochemical reactions Existing methods have found limited use and are not routinely encountered in the production of radiotracers Herein we propose a facile onestep direct 11Cmethylation of cysteine residues in peptides using 11Cmethyl triflate under ambient temperatures 20 °C and short reaction times on the order of seconds Good regioselectivity of this method was demonstrated by HPLC in a simple peptide glutathione GSH and a more complex test decapeptide TrpTyrTrpSerArgCysLysTrpThrGly bearing multiple nucleophilic sites In addition we extend this method towards the synthesis of 11CCysMeTyr3octreotate as a demonstration of applicability for peptides of biological interest This octreotate derivative was obtained in nondecaycorrected radiochemical yields of 11 ± 2  n = 3 with a synthesis time of approx 30 min

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