Document Detail

Diastereoselective Pictet-Spengler approach for the synthesis of pyrrolo[3,2-e][1,4]diazepin-2-one peptide turn mimics.
MedLine Citation:
PMID:  18543989     Owner:  NLM     Status:  MEDLINE    
Sixteen pyrrolo[3,2- e][1,4]diazepin-2-ones 1 were synthesized in 4-5 steps and 5-48% overall yields from 4-oxoproline 8 by a route featuring a diastereoselective Pictet-Spengler reaction to close the seven-membered diazepinone ring. Crystallographic analysis of pyrrolo[3,2- e][1,4]diazepin-2-one 1b by X-ray diffraction demonstrated that the alpha-amino acid residue adopted dihedral angle geometry similar to an ideal gamma-turn, illustrating the potential for employing these novel heterocycles as peptide turn mimics.
Philippe Deaudelin; William D Lubell
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-06-11
Journal Detail:
Title:  Organic letters     Volume:  10     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2008 Jul 
Date Detail:
Created Date:  2008-06-26     Completed Date:  2008-09-16     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2841-4     Citation Subset:  IM    
Département de chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec, Canada, H3C 3J7.
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MeSH Terms
Alkenes / chemistry
Amides / chemistry
Azepines / chemistry*
Biomimetic Materials / chemical synthesis*,  chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Peptides / chemical synthesis*,  chemistry
Pyrroles / chemistry*
Reg. No./Substance:
0/Alkenes; 0/Amides; 0/Azepines; 0/Peptides; 0/Pyrroles

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