Solid-phase synthesis of C-terminally modified peptides

In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles a...

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Bibliographic Details
Published in:Journal of peptide science Vol. 12; no. 11; pp. 686 - 692
Main Authors: Ten Brink, Hefziba T., Meijer, Joris T., Geel, Remon V., Damen, Mark, Löwik, Dennis W. P. M., van Hest, Jan C. M.
Format: Journal Article
Language:English
Published: Chichester, UK John Wiley & Sons, Ltd 01.11.2006
Subjects:
Aldehydes - chemistry
Amines - chemistry
Amino Acid Sequence
Biochemistry - methods
labeled peptides
modified peptides
Molecular Sequence Data
Peptides - chemical synthesis
Polystyrenes - chemistry
reductive amination
Resins, Synthetic - chemistry
solid-phase synthesis
ISSN:1075-2617, 1099-1387
Online Access:Get full text
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Summary:In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.
Bibliography:ark:/67375/WNG-F5SKVN73-D
istex:31CC358D60155CA94003BF9EF5F5D9806995AF41
ArticleID:PSC780
ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ObjectType-Article-1
ObjectType-Feature-2
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.780