Document Detail

Towards a stable α-cycloalkyl amino acid with a photo-switchable cationic side-chain.
MedLine Citation:
PMID:  22239068     Owner:  NLM     Status:  Publisher    
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.
Riccardo Rossi Paccani; Donato Donati; Stefania Fusi; Loredana Latterini; Grazia Farina; Vinicio Zanirato; Massimo Olivucci
Related Documents :
25208488 - Fourier transform infrared spectroscopy for the prediction of fatty acid profiles in mu...
25209638 - Triacylglyceride composition and fatty acyl saturation profile of a psychrophilic and p...
25445568 - Fungal jarosite biomineralization in río tinto.
7772938 - Metabolism of halohydroquinones in rhodococcus chlorophenolicus pcp-1.
12010518 - Relative hydrophobicity of amino acid residues in homooligopeptides as measured by aque...
8483098 - A contribution to the structure-activity relationship in glutamate receptor ligands: 1....
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-1-12
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-1-13     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Potentially inappropriate medication use in Indian elderly: Comparison of Beers' criteria and Screen...
Next Document:  Responses to risk: Public submissions on Australian alcohol guidelines for low-risk drinking.