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
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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
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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
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Volumen: | 18
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Número: | 18
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Página de inicio: | 2190
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Página de fin: | 2196
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DOI: |
http://dx.doi.org/10.1016/j.tetasy.2007.09.010 |
Título revista: | Tetrahedron Asymmetry
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Título revista abreviado: | Tetrahedron Asymmetry
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ISSN: | 09574166
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CODEN: | TASYE
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CAS: | amino acid, 65072-01-7; polyamide, 63428-83-1
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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