NDLI: 2-Methoxy-4-methylsulfinylbenzyl: A Backbone Amide Safety-Catch Protecting Group for the Synthesis and Purification of Difficult Peptide Sequences

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2-Methoxy-4-methylsulfinylbenzyl: A Backbone Amide Safety-Catch Protecting Group for the Synthesis and Purification of Difficult Peptide Sequences

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2-Methoxy-4-methylsulfinylbenzyl: A Backbone Amide Safety-Catch Protecting Group for the Synthesis and Purification of Difficult Peptide Sequences

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Paradís-bas, Marta Tulla-puche, Judit Albericio, Fernando
Description	Author Affiliation: Paradís-Bas M ( Institute for Research in Biomedicine (IRB Barcelona), Baldiri Reixac 10, Barcelona, 08028 (Spain), Fax: (+34) 93-4037126)
Abstract	The use of 2-methoxy-4-methylsulfinylbenzyl (Mmsb) as a new backbone amide-protecting group that acts as a safety-catch structure is proposed. Mmsb, which is stable during the elongation of the sequence and trifluoroacetic acid-mediated cleavage from the resin, improves the synthetic process as well as the properties of the quasi-unprotected peptide. Mmsb offers the possibility of purifying and characterizing complex peptide sequences, and renders the target peptide after $NH_{4}I/TFA$ treatment and subsequent ether precipitation to remove the cleaved Mmsb moiety. First, the “difficult peptide” sequence $H-(Ala)_{10}-NH_{2}$ was selected as a model to optimize the new protecting group strategy. Second, the complex, bioactive $Ac-(RADA)_{4}-NH_{2}$ sequence was chosen to validate this methodology. The improvements in solid-phase peptide synthesis combined with the enhanced solubility of the quasi-unprotected peptides, as compared with standard sequences, made it possible to obtain purified $Ac-(RADA)_{4}-NH_{2}.$ To extend the scope of the approach, the challenging Aβ(1-42) peptide was synthesized and purified in a similar manner. The proposed Mmsb strategy opens up the possibility of synthesizing other challenging small proteins.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	46
Volume Number	20
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2014-11-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Benzyl Compounds Chemistry Peptides Chemical Synthesis Solid-Phase Synthesis Techniques Sulfides Amides Amino Acid Sequence Amyloid Beta-Peptides Molecular Sequence Data Peptide Fragments Trifluoroacetic Acid Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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