| Problem of aspartimide formation in Fmoc-based solid-phase peptide synthesis using Dmab group to protect side chain of aspartic acid. | |
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MedLine Citation:
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PMID: 17975850 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The sequence-dependent, acid- or base-catalysed aspartimide formation is one of the most serious side reactions in solid-phase synthesis of peptides containing aspartic acid. In the present work, we investigated the susceptibility of 4-(N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino)benzyl (Dmab), an aspartic acid beta-carboxy side-chain protecting group, for aspartimide formation. As a model, 15-amino acid-residue galanin fragment analogue containing the Asp-Ala motif was used during Fmoc-based solid-phase synthesis. Our study showed a strong tendency of Dmab-protected peptide to form aspartimide with unusual high efficiency. Furthermore, to investigate the susceptibility of Asp-Ala motif for aspartimide formation during the synthesis using Asp(ODmab), a 5-amino acid-residue galanin fragment LGPDA, different types of resin linkers, variety of Fmoc-deprotection conditions and coupling methods were applied. |
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Authors:
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Jarosław Ruczyński; Brygida Lewandowska; Piotr Mucha; Piotr Rekowski |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of peptide science : an official publication of the European Peptide Society Volume: 14 ISSN: 1075-2617 ISO Abbreviation: J. Pept. Sci. Publication Date: 2008 Mar |
Date Detail:
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Created Date: 2008-02-21 Completed Date: 2008-05-30 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9506309 Medline TA: J Pept Sci Country: England |
Other Details:
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Languages: eng Pagination: 335-41 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland. jarecki@chem.univ.gda.pl |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry* Aspartic Acid / analogs & derivatives*, chemistry Chemistry / methods Fluorenes / chemistry* Isoaspartic Acid / chemistry* Peptides / chemical synthesis*, chemistry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Fluorenes; 0/Isoaspartic Acid; 0/N(alpha)-fluorenylmethyloxycarbonylamino acids; 0/Peptides; 56-84-8/Aspartic Acid; 5615-80-5/aspartimide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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