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
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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:  -    
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