NDLI: Carbon-11 radiolabeling of an oligopeptide containing tryptophan hydrochloride via a Pictet-Spengler reaction using carbon-11 formaldehyde.

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Carbon-11 radiolabeling of an oligopeptide containing tryptophan hydrochloride via a Pictet-Spengler reaction using carbon-11 formaldehyde.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Hanyu, Masayuki Takada, Yuuki Hashimoto, Hiroki Kawamura, Kazunori Zhang, Ming-Rong Fukumura, Toshimitsu
Description	Country affiliation: Japan Author Affiliation: Hanyu M ( Molecular Probe Program, Molecular Imaging Center, National Institute of Radiological Science, 4-9-1 Anagawa, Inage-ku, Chiba, 263-8555, Japan.)
Abstract	A procedure for the synthesis of a(11)C-labeled oligopeptide containing [1-(11)C]1,2,3,4-tetrahydro-ß-carboline-3-carboxylic acid ([1-(11)C]Tpi) from the corresponding Trpâ ¢HCl-containing peptides has been developed involving a Pictet-Spengler reaction with [(11) C]formaldehyde. The synthesis of [1-(11)C]Tpi from Trp and [(11)C]formaldehyde was examined as a model reaction with the aim of developing a facile and effective method for the labeling of peptides with carbon-11. The Pictet-Spengler reaction of Trp and [(11)C]formaldehyde in acidic media (TsOH or HCl) afforded the desired [1-(11)C]Tpi in a moderate radiochemical yield. Herein, the application of a Pictet-Spengler reaction to an aqueous solution of Trpâ ¢HCl gave the desired product with a radiochemical yield of 45.2%. The RGD peptide cyclo[Arg-Gly-Asp-D-Tyr-Lys] was then selected as a substrate for the labeling reaction with [(11)C]formaldehyde. The radiolabeling of a Trpâ ¢HCl-containing RGD peptide using the Pictet-Spengler reaction was successful. Furthermore, the remote-controlled synthesis of a [1-(11)C]Tpi-containing RGD peptide was attempted by using an automatic production system to generate [(11)C]CH3 I. The radiochemical yield of the [1-(11) C]Tpi-containing RGD at the end of synthesis (EOS) was 5.9 ± 1.9% (n = 4), for a total synthesis time of about 35 min. The specific activity was 85.7 ± 9.4 GBq/µmol at the EOS.
File Format	HTM / HTML
ISSN	10752617
Issue Number	10
Volume Number	19
e-ISSN	10991387
Journal	Journal of Peptide Science
Language	English
Publisher	Wiley
Publisher Date	2013-10-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Biochemistry Carbon Radioisotopes Chemistry Molecular Imaging Oligopeptides Chemical Synthesis Tryptophan Carbolines Formaldehyde Humans Positron-emission Tomography Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Structural Biology Medicine Drug Discovery Biochemistry Molecular Biology Pharmacology Molecular Medicine

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