| Direct access to side chain N,N'-diaminoalkylated derivatives of basic amino acids suitable for solid-phase peptide synthesis. | |
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MedLine Citation:
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PMID: 22714010 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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A simple and efficient one-pot procedure that enables rapid access to orthogonally protected N,N'-diaminoalkylated basic amino acid building blocks fully compatible with standard Boc and Fmoc solid-phase peptide synthesis is reported. Described synthetic approach includes double reductive alkylation of N (α)-protected diamino acids with N-protected amino aldehydes in the presence of sodium cyanoborohydride. This approach allows preparation of symmetrical, as well as unsymmetrical, basic amino acid derivatives with branched side-chains that can be further modified, enhancing their synthetic utility. The suitability of the synthesized branched basic amino acid building blocks for use in standard solid-phase peptide synthesis has been demonstrated by synthesis of an indolicidin analogue in which the lysine residue was substituted with the synthetic derivative N ( α )-(9H-fluorenyl-9-methoxycarbonyl)-N ( β ),N ( β ) '-bis[2-(tert-butoxycarbonylamino)ethyl]-L: -2,3-diaminopropionic acid. This substitution resulted in an analogue with more ordered secondary structure in 2,2,2-trifluoroethanol and enhanced antibacterial activity without altering hemolytic activity. |
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Authors:
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Jean-Philippe Pitteloud; Nina Bionda; Predrag Cudic |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-6-20 |
Journal Detail:
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Title: Amino acids Volume: - ISSN: 1438-2199 ISO Abbreviation: - Publication Date: 2012 Jun |
Date Detail:
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Created Date: 2012-6-20 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9200312 Medline TA: Amino Acids Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port St. Lucie, FL, 34987, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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