Abstract:
2-Amino-2,3-dideoxy-d-manno-heptonic acid (7) has been synthesized from 2,5,6,7-tetra-O-acetyl-3-deoxy-d-gluco-heptono-1,4-lactone (1), which was readily prepared from d-glycero-d-gulo-heptono-1,4-lactone. O-Deacetylation of 1 followed by treatment with 13:1 (v/v) 2,2-dimethoxypropane/acetone in the presence of p-toluenesulfonic acid gave methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-d-gluco-heptonate (3) as a crystalline product (80% yield). The free hydroxyl group (OH-2) of 3 was mesylated and substituted by azide to give the corresponding azide derivative 5. Hydrogenolysis and further hydrolysis of the ester function of 5 afforded α-amino acid 7 (43% overall yield from 1). Compound 7 is an analog of l-alanine having a polyhydroxy chain attached to C-3. The diastereoisomer of 7 at C-2, 2-amino-2,3-dideoxy-d-gluco-heptonic acid (12) was also prepared from 3, by a route that involved 2,3-dideoxy-2-iodo derivative 8 as a key intermediate. © 2006 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone |
Autor: | Gómez, R.V.; Kolender, A.A.; 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: | Acetonation; d-Alanine; l-Alanine; Polyhydroxy amino acids; Sugar amino acids; Acetone; Hydrolysis; Organic polymers; Substitution reactions; Synthesis (chemical); Acetonation; d-Alanine; l-Alanine; Polyhydroxy amino acids; Sugar amino acids; Amino acids; acetone; alanine; alpha amino acid; amino acid derivative; azide; dextro alanine; ester; hydroxyl group; lactone derivative; propane; sulfonic acid derivative; amino acid synthesis; article; deacetylation; diastereoisomer; hydrogenolysis; hydrolysis; priority journal; substitution reaction; Alanine; Amino Sugars; Carbohydrate Conformation; Heptoses; Stereoisomerism; Sugar Acids; Gulo; Tetra |
Año: | 2006
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Volumen: | 341
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Número: | 10
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Página de inicio: | 1498
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Página de fin: | 1504
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DOI: |
http://dx.doi.org/10.1016/j.carres.2006.03.028 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | Carbohydr. Res.
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ISSN: | 00086215
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CODEN: | CRBRA
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CAS: | acetone, 67-64-1; alanine, 56-41-7, 6898-94-8; azide, 12596-60-0, 14343-69-2; propane, 74-98-6; Alanine, 56-41-7; Amino Sugars; heptono-1,4-lactone; Heptoses; Sugar Acids
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n10_p1498_Gomez |
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Citas:
---------- APA ----------
Gómez, R.V., Kolender, A.A. & Varela, O.
(2006)
. Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone. Carbohydrate Research, 341(10), 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028---------- CHICAGO ----------
Gómez, R.V., Kolender, A.A., Varela, O.
"Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone"
. Carbohydrate Research 341, no. 10
(2006) : 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028---------- MLA ----------
Gómez, R.V., Kolender, A.A., Varela, O.
"Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone"
. Carbohydrate Research, vol. 341, no. 10, 2006, pp. 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028---------- VANCOUVER ----------
Gómez, R.V., Kolender, A.A., Varela, O. Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone. Carbohydr. Res. 2006;341(10):1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028