An Extended β-Strand Mimic for a Larger Artificial β-Sheet

Autor:	James S. Nowick, Joseph W. Ziller, and Darren L. Holmes, Mason Pairish, In Quen Lee
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Molecular model Tetrapeptide Chemistry Peptidomimetic Stereochemistry Beta sheet Peptide General Chemistry Tripeptide Antiparallel (biochemistry) Biochemistry Combinatorial chemistry Catalysis Colloid and Surface Chemistry Proton NMR
Zdroj:	Journal of the American Chemical Society. 119:5413-5424
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja963843s
Popis:	This paper reports the development of β-strand mimic B, which duplicates the hydrogen-bonding functionality of one edge of a tetrapeptide β-strand. When attached to a tripeptide by a suitable linking group, β-strand mimic B forms a hydrogen-bonded antiparallel β-sheet structure, artificial β-sheet 2. β-Strand mimic B is based upon a 5-hydrazino-2-methoxybenzoic acid building block. The first half of the paper describes synthetic, IR and 1H NMR spectroscopic, X-ray crystallographic, and molecular modeling studies of 5-hydrazino-2-methoxybenzoic acid derivatives and related molecules. These studies establish that hydrazide derivatives of 5-hydrazino-2-methoxybenzoic acid adopt a conformation similar to that of a peptide β-strand and are suitable for use as β-strand mimics. The second half of the paper describes synthetic and 1H NMR spectroscopic studies of artificial β-sheet 2 and of controls 20 and 21, which resemble the peptidomimetic and peptide strands of 2. These experiments indicate that 2 adopts a co...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f53d9efe10dcd81b10be3b6057f8fda6 https://doi.org/10.1021/ja963843s Zobrazit plný text záznamu