| Towards a stable α-cycloalkyl amino acid with a photo-switchable cationic side-chain. | |
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MedLine Citation:
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PMID: 22239068 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The N-alkylated indanyliden-pyrroline (NAIP) Schiff base 3 is an unnatural α-amino acid precursor potentially useful for the preparation of semi-synthetic peptides and proteins incorporating charged side-chains whose structure can be modulated via Z/E photoisomerization. Here we report that the heteroallylic protons of 3 lead to partial loss of ethanol accompanied by formation of the novel heterocyclic system 4 during attempted de-protection. We also show that the same protons catalyze the thermal isomerization of 3 making the light-driven conformational control concept ineffective for times longer than a few hours. These problems are not present in the previously unreported compound 5 where the acidic methyl group is replaced by a H atom. Therefore 5, rather than 3, constitutes a promising prototype for the design of building-blocks capable to modulate the electrostatic potential of a protein in specific locations via light irradiation. |
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Authors:
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Riccardo Rossi Paccani; Donato Donati; Stefania Fusi; Loredana Latterini; Grazia Farina; Vinicio Zanirato; Massimo Olivucci |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-1-12 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Jan |
Date Detail:
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Created Date: 2012-1-13 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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