The synthesis ofsyn- andanti-2(S)-phthalimido-methyl-2,3,4,4a,7,7a-hexahydro-6-oxo-5H-pyrano-[2,3-b]pyrroles as rigid β-bend peptide-mimetics

Autor:	John L. Krstenansky, Bruce L. Currie, Michelle del Rosario-Chow
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Stereochemistry Sodium Organic Chemistry chemistry.chemical_element Peptide Alkylation High-performance liquid chromatography Amino acid chemistry.chemical_compound chemistry Lactam Leucine Pyrrole
Zdroj:	Journal of Heterocyclic Chemistry. 29:707-711
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570290406
Popis:	The synthesis of the syn- 14 and anti- 13 isomers of 2(S)-phthalimidornethyl-2,3,4,4a,7,7a-hexahydro-6-oxo-5H-pyrano[2,3-b]pyrrole was accomplished starting from sodium 3,4-dihydro-2H-pyran-2-carboxylate. The isomers were separated by preparative high performance liquid chromatography. Both isomers can serve as β-bend mimetics and represent three amino acids plus the amino group of the fourth amino acid of a peptide. The lactam nitrogen was alkylated to provide the equivalent of a leucine as the fourth amino acid residue.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c84dda51a707dffb989a7c4824b521d6 https://doi.org/10.1002/jhet.5570290406 Zobrazit plný text záznamu Plný text