메뉴 건너뛰기




Volumn 8, Issue , 2012, Pages 1134-1143

Synthesis of 4" manipulated Lewis X trisaccharide analogues

Author keywords

Chlorodeoxygalactose; Fluorodeoxygalactose; Lewis X analogues; Oligosaccharide synthesis

Indexed keywords


EID: 84864754051     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.8.126     Document Type: Article
Times cited : (8)

References (76)
  • 10
    • 0028174246 scopus 로고
    • doi:10.1002/jnr.490370406
    • Satoh, J.; Kim, S. U. J. Neurosci. Res. 1994, 37, 466-474. doi:10.1002/jnr.490370406
    • (1994) J. Neurosci. Res , vol.37 , pp. 466-474
    • Satoh, J.1    Kim, S.U.2
  • 12
    • 0037403608 scopus 로고    scopus 로고
    • Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively
    • DOI 10.1016/S0008-6215(03)00053-3
    • Asnani, A.; Auzanneau, F.-I. Carbohydr. Res. 2003, 338, 1045-1054. doi:10.1016/S0008-6215(03)00053-3 (Pubitemid 36428837)
    • (2003) Carbohydrate Research , vol.338 , Issue.10 , pp. 1045-1054
    • Asnani, A.1    Auzanneau, F.-I.2
  • 13
    • 46549083255 scopus 로고    scopus 로고
    • doi:10.1016/j.carres.2008.04.017
    • Asnani, A.; Auzanneau, F.-I. Carbohydr. Res. 2008, 343, 1653-1664. doi:10.1016/j.carres.2008.04.017
    • (2008) Carbohydr. Res , vol.343 , pp. 1653-1664
    • Asnani, A.1    Auzanneau, F.-I.2
  • 22
    • 0000523048 scopus 로고
    • doi:10.1351/pac198961071171
    • Bundle, D. R. Pure Appl. Chem. 1989, 61, 1171-1180. doi:10.1351/ pac198961071171
    • (1989) Pure Appl. Chem , vol.61 , pp. 1171-1180
    • Bundle, D.R.1
  • 23
    • 0025074797 scopus 로고
    • O-antigen biotin conjugates. Preparation and use in direct competitive enzyme immunoassays
    • DOI 10.1016/0022-1759(90)90037-V
    • Meikle, P. J.; Young, N. M.; Bundle, D. R. J. Immunol. Methods 1990, 132, 255-261. doi:10.1016/0022-1759(90)90037-V (Pubitemid 20281885)
    • (1990) Journal of Immunological Methods , vol.132 , Issue.2 , pp. 255-261
    • Meikle, P.J.1    Young, N.M.2    Bundle, D.R.3
  • 25
    • 0004285044 scopus 로고    scopus 로고
    • Recognition of carbohydrate antigens by antibody binding sites. in
    • Hecht, S M., Ed.; Oxford University Press: New York
    • Bundle, D. R. Recognition of Carbohydrate Antigens by Antibody Binding Sites. In Bioorganic Chemistry: Carbohydrates; Hecht, S. M., Ed.; Oxford University Press: New York, 1999; pp 370-440.
    • (1999) Bioorganic Chemistry: Carbohydrates , pp. 370-440
    • Bundle, D.R.1
  • 26
    • 0003012148 scopus 로고    scopus 로고
    • doi:10.1021/ar9600087
    • Lemieux, R. U. Acc. Chem. Res. 1996, 29, 373-380. doi:10.1021/ar9600087
    • (1996) Acc. Chem. Res , vol.29 , pp. 373-380
    • Lemieux, R.U.1
  • 27
    • 0031935175 scopus 로고    scopus 로고
    • Computational carbohydrate chemistry: What theoretical methods can tell us
    • DOI 10.1023/A:1006984709892
    • Woods, R. J. Glycoconjugate J. 1998, 15, 209-216. doi:10.1023/A: 1006984709892 (Pubitemid 28121372)
    • (1998) Glycoconjugate Journal , vol.15 , Issue.3 , pp. 209-216
    • Woods, R.J.1
  • 34
    • 0026832946 scopus 로고
    • doi:10.1016/0008-6215(92)84057-Y
    • Jain, R. K.; Matta, K. L. Carbohydr. Res. 1992, 226, 91-100. doi:10.1016/0008-6215(92)84057-Y
    • (1992) Carbohydr. Res , vol.226 , pp. 91-100
    • Jain, R.K.1    Matta, K.L.2
  • 37
    • 0029904583 scopus 로고    scopus 로고
    • b, and Le(x) using a standard set of reaction conditions
    • DOI 10.1021/ja9608555
    • Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239-9248. doi:10.1021/ja9608555 (Pubitemid 26355117)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.39 , pp. 9239-9248
    • Yan, L.1    Kahne, D.2
  • 38
    • 0031689853 scopus 로고    scopus 로고
    • Synthesis of N-acetylglucosamine containing Lewis A and Lewis X building blocks based on N-tetrachlorophthaloyl protection - Synthesis of Lewis X pentasaccharide
    • DOI 10.1016/S0008-6215(98)00148-7, PII S0008621598001487
    • Lay, L.; Manzoni, L.; Schmidt, R. R. Carbohydr. Res. 1998, 310, 157-171. doi:10.1016/S0008-6215(98)00148-7 (Pubitemid 28461917)
    • (1998) Carbohydrate Research , vol.310 , Issue.3 , pp. 157-171
    • Lay, L.1    Manzoni, L.2    Schmidt, R.R.3
  • 40
    • 0032825690 scopus 로고    scopus 로고
    • Active-latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses
    • DOI 10.1016/S0008-6215(99)00080-4, PII S0008621599000804
    • Cao, S.; Gan, Z.; Roy, R. Carbohydr. Res. 1999, 318, 75-81. doi:10.1016/S0008-6215(99)00080-4 (Pubitemid 29421785)
    • (1999) Carbohydrate Research , vol.318 , Issue.1-4 , pp. 75-81
    • Cao, S.1    Gan, Z.2    Roy, R.3
  • 43
    • 0034684254 scopus 로고    scopus 로고
    • doi:10.1021/ja001930l
    • Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223. doi:10.1021/ja001930l
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 10222-10223
    • Zhu, T.1    Boons, G.-J.2
  • 44
    • 0035354657 scopus 로고    scopus 로고
    • doi:10.1002/1521-3765(20010601)7:112382::AID-CHEM238203.0.C O;2-2
    • Zhu, T.; Boons, G.-J. Chem.-Eur. J. 2001, 7, 2382-2389. doi:10.1002/1521-3765(20010601)7:113.0.C O;2-2
    • (2001) Chem.-Eur. J , vol.7 , pp. 2382-2389
    • Zhu, T.1    Boons, G.-J.2
  • 45
    • 0037014993 scopus 로고    scopus 로고
    • Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series
    • DOI 10.1016/S0008-6215(02)00164-7, PII S0008621502001647
    • La Ferla, B.; Prosperi, D.; Lay, L.; Giovanni, R.; Panza, L. Carbohydr. Res. 2002, 337, 1333-1342. doi:10.1016/S0008-6215(02)00164-7 (Pubitemid 35247507)
    • (2002) Carbohydrate Research , vol.337 , Issue.15 , pp. 1333-1342
    • La Ferla, B.1    Prosperi, D.2    Lay, L.3    Russo, G.4    Panza, L.5
  • 48
    • 0026786640 scopus 로고
    • doi:10.1016/S0040-4039(00)79122-2
    • Toepfer, A.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161-5164. doi:10.1016/S0040-4039(00)79122-2
    • (1992) Tetrahedron Lett , vol.33 , pp. 5161-5164
    • Toepfer, A.1    Schmidt, R.R.2
  • 49
    • 0031575629 scopus 로고    scopus 로고
    • A versatile synthesis of the lactoneo-series antigens synthesis of sialyl dimer Lewis X and of dimer Lewis Y
    • DOI 10.1016/S0040-4039(97)00006-3, PII S0040403997000063
    • Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173-1176. doi:10.1016/S0040-4039(97)00006-3 (Pubitemid 27076175)
    • (1997) Tetrahedron Letters , vol.38 , Issue.7 , pp. 1173-1176
    • Hummel, G.1    Schmidt, R.R.2
  • 50
    • 0032482294 scopus 로고    scopus 로고
    • Large scale synthesis of linker-modified sialyl Lewis(X), Lewis(X) and N-acetyllactosamine
    • DOI 10.1016/S0040-4020(98)00294-4, PII S0040402098002944
    • Kretzschmar, G.; Stahl, W. Tetrahedron 1998, 54, 6341-6358. doi:10.1016/S0040-4020(98)00294-4 (Pubitemid 28231248)
    • (1998) Tetrahedron , vol.54 , Issue.23 , pp. 6341-6358
    • Kretzschmar, G.1    Stahl, W.2
  • 54
    • 0028007407 scopus 로고
    • doi:10.1016/0040-4039(94)80013-8
    • Windmüller, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 7927-7930. doi:10.1016/0040-4039(94)80013-8
    • (1994) Tetrahedron Lett , vol.35 , pp. 7927-7930
    • Windmüller, R.1    Schmidt, R.R.2
  • 56
    • 0022426354 scopus 로고
    • doi:10.1016/0008-6215(85)90011-4
    • Lönn, H. Carbohydr. Res. 1985, 139, 105-113. doi:10.1016/0008- 6215(85)90011-4
    • (1985) Carbohydr. Res , vol.139 , pp. 105-113
    • Lönn, H.1
  • 62
  • 64
  • 65
    • 0034835601 scopus 로고    scopus 로고
    • Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers
    • DOI 10.1021/ja010086b
    • Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2001, 123, 6819-6825. doi:10.1021/ja010086b (Pubitemid 32884542)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.28 , pp. 6819-6825
    • Crich, D.1    Dudkin, V.2
  • 66
    • 0141631599 scopus 로고    scopus 로고
    • Glycosylation of N-acetylglucosamine: Imidate formation and unexpected conformation
    • DOI 10.1021/ol034669x
    • Liao, L.; Auzanneau, F.-I. Org. Lett. 2003, 5, 2607-2610. doi:10.1021/ol034669x (Pubitemid 37140822)
    • (2003) Organic Letters , vol.5 , Issue.15 , pp. 2607-2610
    • Liao, L.1    Auzanneau, F.-I.2
  • 69
    • 77953136893 scopus 로고    scopus 로고
    • doi:10.1016/j.carres.2010.03.038
    • Wang, A.; Auzanneau, F.-I. Carbohydr. Res. 2010, 345, 1216-1221. doi:10.1016/j.carres.2010.03.038
    • (2010) Carbohydr. Res , vol.345 , pp. 1216-1221
    • Wang, A.1    Auzanneau, F.-I.2
  • 70
    • 23044512549 scopus 로고    scopus 로고
    • The amide group in N-acetylglucosamine glycosyl acceptors affects glycosylation outcome
    • DOI 10.1021/jo050707+
    • Liao, L.; Auzanneau, F.-I. J. Org. Chem. 2005, 70, 6265-6273. doi:10.1021/jo050707+ (Pubitemid 41076509)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.16 , pp. 6265-6273
    • Liao, L.1    Auzanneau, F.-I.2
  • 72
    • 28444444841 scopus 로고    scopus 로고
    • Unusual conformational behavior of trisaccharides containing N-acetylglucosamine
    • DOI 10.1016/j.carres.2005.09.025, PII S0008621505004659
    • Liao, L.; Robertson, V.; Auzanneau, F.-I. Carbohydr. Res. 2005, 340, 2826-2832. doi:10.1016/j.carres.2005.09.025 (Pubitemid 41735372)
    • (2005) Carbohydrate Research , vol.340 , Issue.18 , pp. 2826-2832
    • Liao, L.1    Robertson, V.2    Auzanneau, F.-I.3
  • 73
    • 33646495939 scopus 로고    scopus 로고
    • doi:10.1016/j.carres.2006.04.007
    • Ruttens, B.; Ková?, P. Carbohydr. Res. 2006, 341, 1077-1080. doi:10.1016/j.carres.2006.04.007
    • (2006) Carbohydr. Res , vol.341 , pp. 1077-1080
    • Ruttens, B.1    Ková, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.