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Abstract:

Two regioisomeric and stereoregular AABB-type polyamides have been synthesized using l-glutamic acid 1 and l-alaninol 4 as sources of chirality. From 4, two derivatives of chiral diamines were prepared and regioselectively condensed with pentachlorophenyl 5-oxo-(S)-2-tetrahydrofurancarboxylate 3, derived from 1. Manipulation of functional groups and convenient deprotections led to the ammonium salts of N-[1′-amino-(S)-2′-propyl]- and N-[(S)-2′-amino-1′-propyl]-5-oxo-(S)-2-tetrahydrofurancarboxyamide 11 and 15, respectively, in which the building blocks derived from 1 and 4 are linked through an amido group. Compounds 11 and 15 are, in fact, α,ω-amino acids having amino and lactone groups, and hence activated for polycondensation. Thus, polymerization of 11 took place under regio- and stereo-control to afford stereoregular poly[N-(1′-amino-(S)-2′-propyl)-carboxyamido-(S)-2-hydroxypentan-5-oic acid] (16). Similar polycondensation of 15, under the optimized conditions employed for the synthesis of 16, gave the regioisomeric polyamide 17, which exhibited a molecular weight lower than that of 16. The thermal and spectroscopic properties of optically active AABB-polyamides 16 and 17 are described. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids
Autor:Gómez, R.V.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:acid; amino acid; ammonium derivative; diamine derivative; lactone derivative; poly[n (1' amino 2' propyl)carboxyamido 2 hydroxypentan 5 oic acid]; polyamide; unclassified drug; article; carbon nuclear magnetic resonance; chirality; deprotection reaction; hydrogenation; polymerization; priority journal; proton nuclear magnetic resonance; stereochemistry; synthesis
Año:2007
Volumen:18
Número:18
Página de inicio:2190
Página de fin:2196
DOI: http://dx.doi.org/10.1016/j.tetasy.2007.09.010
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:amino acid, 65072-01-7; polyamide, 63428-83-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v18_n18_p2190_Gomez

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Citas:

---------- APA ----------
Gómez, R.V. & Varela, O. (2007) . Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids. Tetrahedron Asymmetry, 18(18), 2190-2196.
http://dx.doi.org/10.1016/j.tetasy.2007.09.010
---------- CHICAGO ----------
Gómez, R.V., Varela, O. "Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids" . Tetrahedron Asymmetry 18, no. 18 (2007) : 2190-2196.
http://dx.doi.org/10.1016/j.tetasy.2007.09.010
---------- MLA ----------
Gómez, R.V., Varela, O. "Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids" . Tetrahedron Asymmetry, vol. 18, no. 18, 2007, pp. 2190-2196.
http://dx.doi.org/10.1016/j.tetasy.2007.09.010
---------- VANCOUVER ----------
Gómez, R.V., Varela, O. Synthesis of regioisomeric, stereoregular AABB-type polyamides from chiral diamines and diacids derived from natural amino acids. Tetrahedron Asymmetry. 2007;18(18):2190-2196.
http://dx.doi.org/10.1016/j.tetasy.2007.09.010