Tyrosine alkyl esters as prodrug: the structure and intermolecular interactions of l-tyrosine methyl ester compared to l-tyrosine and its ethyl and n-butyl esters

Autor: Ivo B. Rietveld, Maria Barrio, Josep-Lluis Tamarit, Nathalie Mahé, Béatrice Nicolaï, René Céolin
Rok vydání: 2011
Předmět:
Zdroj: Structural Chemistry. 22:649-659
ISSN: 1572-9001
1040-0400
DOI: 10.1007/s11224-010-9723-6
Popis: l-Tyrosine alkyl esters are used as prodrugs for l-tyrosine. Although prodrugs are often designed for their behavior in solution, understanding their solid-state properties is the first step in mastering drug delivery. The crystal structure of l-tyrosine methyl ester has been determined and compared to published structures of l-tyrosine and its ethyl and n-butyl esters. It is almost isostructural with the other esters: it crystallizes in the orthorhombic chiral space group P212121, a = 5.7634(15) A, b = 12.111(2) A, c = 14.3713(19) A, V = 1003.1(4) A3 with Z′ = 1. Their main packing motif is a C(9) infinite hydrogen-bond chain, but the conformation of l-tyrosine methyl ester is different from the other two: eclipsed versus U-shaped, respectively. The published structure of the ethyl ester, which was incomplete, has been confirmed by X-ray powder diffraction data. Because l-tyrosine methyl ester is very stable (28 years stored at room temperature), and its hydrolysis rate is relatively low, it should be one of the better prodrugs among the alkyl esters of tyrosine.
Databáze: OpenAIRE
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