An efficient synthesis of two monosulfated trisaccharides with the Galβ1,3GlcNAcβ1,3Galβ-O-Allyl backbone
作者： Jie Xia , Conrad F. Piskorz , Robert D. Locke , E.V. Chandrasekaran , James L. Alderfer
DOI: 10.1016/S0960-894X(99)00507-7
关键词:
摘要: Abstract The GlcNAcβ(1→3) Gal linked disaccharide 7 was synthesized as key building blocks for the construction of target monosulfated trisaccharides 1 and 2 using oxazoline 3 glycosyl donor promoted by BF ·Et O
elsevier.com
sci-hub.se 参考文章(20)
K.L. Matta, O.P. Bahl, Synthesis of enzyme substrates Carbohydrate Research. ,vol. 21, pp. 460- 464 ,(1972) , 10.1016/S0008-6215(00)84929-0
G Lamblin, J M Lo-Guidice, J Lemoine, A Verbert, P Roussel, J M Wieruszeski, Sialylation and sulfation of the carbohydrate chains in respiratory mucins from a patient with cystic fibrosis. Journal of Biological Chemistry. ,vol. 269, pp. 18794- 18813 ,(1994) , 10.1016/S0021-9258(17)32238-X
Luigi Lay, Luigi Panza, Giovanni Russo, Diego Colombo, Fiamma Ronchetti, Elena Adobati, Silvana Canevari, Oligosaccharides related to tumor‐associate antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide β‐D‐Galp‐(1→3)‐β‐D‐GalpNAc‐(1→3)‐α‐D‐Galp and of the Tetrasaccharide α‐L‐Fucp‐(1→2)‐β‐D‐Galp‐(1→3)‐β‐D‐GalpNAc‐(1→3)‐α‐D‐Galp, components of a tumor antigen recognized by the antibody MBr1 Helvetica Chimica Acta. ,vol. 78, pp. 533- 538 ,(1995) , 10.1002/HLCA.19950780302
Oliver Seitz, Chi-Huey Wong, Chemoenzymatic Solution- and Solid-Phase Synthesis ofO-Glycopeptides of the Mucin Domain of MAdCAM-1. A General Route toO-LacNAc,O-Sialyl-LacNAc, andO-Sialyl-Lewis-X Peptides Journal of the American Chemical Society. ,vol. 119, pp. 8766- 8776 ,(1997) , 10.1021/JA971383C
Wolf Peter Stöckl, Hans Weidmann, Synthesen und Reaktionen von 1,2-Didesoxy-Hexopyrano-[2,1-d]-Oxazolinen und -Oxazoliniumsalzen1,2 Journal of Carbohydrate Chemistry. ,vol. 8, pp. 169- 198 ,(1989) , 10.1080/07328308908048003
Calliope Capon, Jean-Michel Wieruszeski, Jerome Lemoine, James C. Byrd, Hakon Leffler, Young S. Kim, Sulfated Lewis X Determinants as a Major Structural Motif in Glycans from LS174T-HM7 Human Colon Carcinoma Mucin Journal of Biological Chemistry. ,vol. 272, pp. 31957- 31968 ,(1997) , 10.1074/JBC.272.51.31957
Gemma Arsequell, Lorely Krippner, Raymond A. Dwek, Simon Y. C. Wong, Building blocks for solid-phase glycopeptide synthesis: 2-acetamido-2-deoxy-β-D-glycosides of FmocSerOH and FmocThrOH Journal of The Chemical Society, Chemical Communications. pp. 2383- 2384 ,(1994) , 10.1039/C39940002383
William J. Sanders, David D. Manning, Kathryn M. Koeller, Laura L. Kiessling, Synthesis of sulfated trisaccharide ligands for the selectins Tetrahedron. ,vol. 53, pp. 16391- 16422 ,(1997) , 10.1016/S0040-4020(97)01024-7
Tomoya Ogawa, Kazuo Beppu, Satoru Nakabayashi, Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis Carbohydrate Research. ,vol. 93, ,(1981) , 10.1016/S0008-6215(00)80765-X
Jean-Claude Jacquinet, Sergei E. Zurabyan, Anatoly Ya. Khorlin, Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides. Glycosylation with 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyrano)-[2′,1′:4,5]-2-oxazoline Carbohydrate Research. ,vol. 32, pp. 137- 143 ,(1974) , 10.1016/S0008-6215(00)82470-2