Document Detail

Self-assembly of noncyclic bis-D- and L-tripeptides into higher order tubular constructs: design, synthesis, and X-ray crystal superstructure.
MedLine Citation:
PMID:  18062697     Owner:  NLM     Status:  MEDLINE    
Trans (1R,2R)-diaminocyclohexane was used as a semirigid vicinal diamine to anchor two N-protected tripeptides consisting of L-D-L amino acids as carboxy terminal amides. The bis-tripeptide consisting of L-Ser (OBn)-D-Ser (OBn)-L-Ser (O-p-bromobenzyl) Boc afforded X-ray quality crystals containing benzene and chloroform solvent molecules. Analysis of the solid-state structure revealed a highly H-bonded helical open-ended tubular superstructure. The tripeptide strands intertwine like a pair of self-embracing arms, held together by a gamma-turn and a 14-membered antiparallel H-bonded macroring spanning the first and third amino acid residues within each strand. Whereas the tripeptide from the R,R anchor gave beautiful crystals from benzene and chloroform, the analogous construct from the S,S-anchored diamine gave a gel. Related bis-tripeptides with different amino acids showed extensive intramolecular H-bonding based on NMR titration and dilution experiments.
Stephen Hanessian; Valerio Vinci; Kamal Fettis; Thierry Maris; Minh Tan Phan Viet
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-12-07
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Feb 
Date Detail:
Created Date:  2008-02-08     Completed Date:  2008-05-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1181-91     Citation Subset:  IM    
Department of Chemistry, Université de Montréal, PO Box 6128, Station Centre-ville, Montréal, QC, H3C 3J7, Canada.
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MeSH Terms
Crystallography, X-Ray
Models, Molecular
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides / chemical synthesis,  chemistry*
Protein Conformation
Spectrometry, Mass, Fast Atom Bombardment
Spectroscopy, Fourier Transform Infrared
Reg. No./Substance:

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