Abstract:
Dicyclohexylcarbodiimide-promoted self-condensation of 2,3:4,5-di-O-isopropylidene-d-galactonic acid (3) led to the macrocyclic oligomeric cyclo[(2,3:4,5-di-O-isopropylidene-(1→6)-d-galactonate)2 ] (4) and cyclo[(2,3:4,5-di-O-isopropylidene-(1→6)-d-galactonate)3 ] (5), having, respectively, 14- and 21-membered rings. The macrocycles 4 and 5 were also synthesized by cyclization of the respective linear dimer 11 and trimer 14 ω-hydroxy acids precursors prepared by stepwise additions of 3. Compounds 4 and 5 are biomaterials that may be described as macrolactone-cyclodextrins. © 2009 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Cyclic oligomers (macroaldonolactones) from a protected d-galactonic acid monomer |
Autor: | Lorena Romero Zaliz, C.; Varela, O. |
Filiación: | CIHIDECAR, CONICET, Departamento de Química Orgánica, Pabellón II, 1428-Buenos Aires, Argentina
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Palabras clave: | Aldonic acid; Biomaterial; Cyclodextrin; Macrocycle; Macrolactone; 2,3:4,5 di o isopropylidene dextro galactonic acid; biomaterial; cyclo[(2,3:4,5 di o isopropylidene 2(1-6) dextro galactonate)]; cyclo[(2,3:4,5 di o isopropylidene 3(1-6) dextro galactonate)]; cyclodextrin; galactonic acid; lactone derivative; macroaldonolactone derivative; macrocyclic compound; oligomer; unclassified drug; article; cyclization; dimerization; oligomerization; proton nuclear magnetic resonance; reaction analysis; synthesis |
Año: | 2009
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Volumen: | 50
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Número: | 40
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Página de inicio: | 5677
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Página de fin: | 5680
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DOI: |
http://dx.doi.org/10.1016/j.tetlet.2009.07.123 |
Título revista: | Tetrahedron Letters
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Título revista abreviado: | Tetrahedron Lett.
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ISSN: | 00404039
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CODEN: | TELEA
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CAS: | cyclodextrin, 12619-70-4; galactonic acid, 13382-27-9
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v50_n40_p5677_LorenaRomeroZaliz |
Referencias:
- Crini, G., (2005) Prog. Polym. Sci., 30, pp. 38-70
- Hebeish, A., Fouda, M.M.G., Hamdy, S.M., El-Sawy, S.M., Abdel-Mohdy, F.A., (2008) Carbohydr. Polym., 74, pp. 268-273
- Higashi, T., Hirayama, F., Misumi, S., Arima, H., Uekama, K., (2008) Biomaterials, 29, pp. 3866-3871
- Li, J., Loh, X.J., (2008) Adv. Drug Delivery Rev., 60, pp. 1000-1017
- Fukuda, M., Miller, D.A., Peppas, N.A., McGinity, J.W., (2008) Int. J. Pharm., 350, pp. 188-196
- Appelt, H.R., Limberger, J.B., Weber, M., Rodrigues, O.E.D., Oliveira, J.S., Lüdtke, D., Braga, A.L., (2008) Tetrahedron Lett., 49, pp. 4956-4957
- Nagashima, I., Shimizu, H., Matsushita, T., Nishimura, S.-I., (2008) Tetrahedron Lett., 49, pp. 3413-3418
- Götsch, A., Mariussen, E., Von der Recke, R., Herzke, D., Berger, U., Vetter, W., (2005) J. Chromatogr., A, 1063, pp. 193-199
- Liberto, E., Cagliero, C., Sgorbini, B., Bicchi, C., Sciarrone, D., D'Acampora Zellner, B., Mondello, L., Rubiolo, P., (2008) J. Chromatogr., A, 1195, pp. 117-126
- Qi Wang, R., Teng Ong, T., Choon Ng, S., (2008) J. Chromatogr., A, 1203, pp. 185-192
- Gattuso, G., Nepogodiev, S.S., Stoddart, J.F., (1998) Chem. Rev., 98, pp. 1919-1958
- Takahashi, S., Souma, K., Hashimoto, R., Koshino, H., Nakata, T., (2004) J. Org. Chem., 69, pp. 4509-4515
- Fürstner, A., Ruiz Caro, J., Prinz, H., Waldmann, H., (2004) J. Org. Chem., 69, pp. 459-467
- Fürstner, A., Albert, M., Mlynarski, J., Matheu, M., DeClercq, E., (2003) J. Am. Chem. Soc., 125, pp. 13132-13142
- Bailliez, V., Figueiredo, R.M., Olesker, A., Cleophax, J., (2003) Tetrahedron Lett., 44, pp. 9151-9153
- Kricheldorf, H.R., Chatti, S., Schwarz, G., Krüger, R.-P., (2003) J. Polym. Sci., Part A: Polym. Chem., 41, pp. 3414-3424
- Culkin, D.A., Jeong, W., Csihony, S., Gomez, E.D., Balsara, N.P., Hedrick, J.L., Waymouth, R.M., (2007) Angew. Chem., Int. Ed., 46, pp. 2627-2630
- Chisholm, M.H., Galucci, J.C., Yin, H., (2006) Proc. Natl. Acad. U.S.A., 103, pp. 15315-15320. , and references therein
- Tang, M., White, A.J.P., Stevens, M.M., Williams, C.K., (2009) Chem. Commun., pp. 941-943
- Romero Zaliz, C.L., Varela, O., (2001) J. Carbohydr. Chem., 20, pp. 689-701
- Romero Zaliz, C.L., Varela, O., (2003) Tetrahedron: Asymmetry, 14, pp. 2579-2586
- Romero Zaliz, C.L., Varela, O., (2005) Tetrahedron: Asymmetry, 16, pp. 97-103
- RomeroZaliz, C.L., Erra-Balsells, R., Nonami, H., Sato, Y., Varela, O., (2005) ARKIVOC, PART xii, pp. 76-87
- Long, D.D., Stetz, R.J.E., Nash, R.J., Marquess, D.G., Lloyd, J.D., Winters, A.L., Asano, N., Fleet, G.W.J., (1999) J. Chem. Soc., Perkin Trans. I, 8, pp. 901-908
- Mayes, B.A., Stetz, R.J.E., Watterson, M.P., Edwards, A.A., Ansell, C.W.G., Tranter, G.E., Fleet, G.W.J., (2004) Tetrahedron: Asymmetry, 15, pp. 627-638
- Parenty, A., Moreau, X., Campagne, J.-M., (2006) Chem. Rev., 106, pp. 911-939
- note; note; Boden, E.P., Keck, G.E., (1985) J. Org. Chem., 50, pp. 2394-2395
- Stork, G., Rychnovsky, S.D., (1987) J. Am. Chem. Soc., 109, pp. 1565-1567
- Zhang, Y., Boyer, R., Sun, X., Paschal, J., Chen, S.-H., (2000) Bioorg. Med. Chem. Lett., 10, pp. 775-778
- Nakagawa, Y., Irie, K., Nakamura, Y., Ohigashi, H., (2001) Bioorg. Med. Chem. Lett., 11, pp. 723-728
Citas:
---------- APA ----------
Lorena Romero Zaliz, C. & Varela, O.
(2009)
. Cyclic oligomers (macroaldonolactones) from a protected d-galactonic acid monomer. Tetrahedron Letters, 50(40), 5677-5680.
http://dx.doi.org/10.1016/j.tetlet.2009.07.123---------- CHICAGO ----------
Lorena Romero Zaliz, C., Varela, O.
"Cyclic oligomers (macroaldonolactones) from a protected d-galactonic acid monomer"
. Tetrahedron Letters 50, no. 40
(2009) : 5677-5680.
http://dx.doi.org/10.1016/j.tetlet.2009.07.123---------- MLA ----------
Lorena Romero Zaliz, C., Varela, O.
"Cyclic oligomers (macroaldonolactones) from a protected d-galactonic acid monomer"
. Tetrahedron Letters, vol. 50, no. 40, 2009, pp. 5677-5680.
http://dx.doi.org/10.1016/j.tetlet.2009.07.123---------- VANCOUVER ----------
Lorena Romero Zaliz, C., Varela, O. Cyclic oligomers (macroaldonolactones) from a protected d-galactonic acid monomer. Tetrahedron Lett. 2009;50(40):5677-5680.
http://dx.doi.org/10.1016/j.tetlet.2009.07.123