NXO building blocks for backbone modification of peptides and preparation of pseudopeptides.
J Org Chem
; 75(8): 2492-500, 2010 Apr 16.
Article
en En
| MEDLINE
| ID: mdl-20297824
ABSTRACT
The design and synthesis of novel building blocks for peptide modification, termed "NXO", is reported. We describe the utility of these building blocks to prepare new pseudo- and oligopeptides and demonstrate the efficient assembly of modified tripeptides using both conventional liquid phase peptide synthesis and solid supported synthesis. Pertaining to the study of NXO in peptide mimicry, the structure of NXO-incorporating tripeptide beta-strand mimics was investigated in the N(L)AlaO incorporating beta-sheet model compound 13. Evidenced by spectroscopy and computation, 13 selectively adopts a beta-structure in chloroform and characteristically samples the NXO-modified backbone site in the core beta-sheet region. ROESY (HNMR) and molecular dynamics data suggest that when disrupting the cross-strand hydrogen-bonding pattern by switching the solvent from CDCl(3) to d(3)-MeOH, the main conformation with peptide and NXO-peptide backbones similar to that in root mean square deviation of corresponding backbone atoms (rmsd) is preserved.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Péptidos
/
Diseño de Fármacos
Tipo de estudio:
Prognostic_studies
Idioma:
En
Revista:
J Org Chem
Año:
2010
Tipo del documento:
Article
País de afiliación:
Austria