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Volumn 110, Issue 9, 2010, Pages 4949-4977

Calixarene and calixresorcarene glycosides: Their synthesis and biological applications

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; ANOMERIC LINKAGES; BIOLOGICAL APPLICATIONS; BIOLOGICAL STUDIES; CALIXARENES; CARBOHYDRATE CLUSTERS; CLUSTER EFFECTS; MACROCYCLES; MACROCYCLICS; REDUCING REAGENTS; TETRAZOLES;

EID: 77954627841     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100027b     Document Type: Article
Times cited : (211)

References (140)
  • 1
    • 77956479715 scopus 로고    scopus 로고
    • Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Hart, G. W., and Marth, J., Eds.; Cold Spring Harbor Laboratory Press: New York,; Chapters 8 and 17.
    • Marth, J., Lowe, B., and Varki, A. In Essentials of Glycobiology; Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Hart, G. W., and Marth, J., Eds.; Cold Spring Harbor Laboratory Press: New York, 1999; Chapters 8 and 17.
    • (1999) Essentials of Glycobiology
    • Marth, J.1    Lowe, B.2
  • 16
    • 77956466853 scopus 로고    scopus 로고
    • note
    • 1H NMR signals for the equatorial and axial protons of the methylene bridges as well resolved doublets at σ ∼3 and σ ∼4, respectively. Moreover, the signals for the carbon atoms of the methylene groups connecting two adjacents phenyl rings in a syn orientation (e.g. in the cone conformation) appear at σ ∼31.
  • 18
    • 21244492862 scopus 로고
    • The n -propylation of the lower rim hydroxy groups inhibits the oxygen-through-the-annulus-rotation and allows the isolation of the blocked cone conformational isomer. See
    • The n -propylation of the lower rim hydroxy groups inhibits the oxygen-through-the-annulus-rotation and allows the isolation of the blocked cone conformational isomer. See: Iwamoto, K., Araki, K., and Shinkai, S. J. Org. Chem. 1991, 56, 4955
    • (1991) J. Org. Chem. , vol.56 , pp. 4955
    • Iwamoto, K.1    Araki, K.2    Shinkai, S.3
  • 19
    • 77956481254 scopus 로고    scopus 로고
    • note
    • 6.
  • 20
    • 77956473558 scopus 로고    scopus 로고
    • note
    • For a review outlining the most common lectins and their carbohydrate-binding partners, see
  • 32
    • 77956494750 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 37
    • 77956481253 scopus 로고    scopus 로고
    • note
    • While this negative result was ascribed to steric factors by the authors, we believe that the open-chain imino form of glycosamines is more likely to be responsible for their low nucleophilicity. Another reasonable possibility is the in situ transformation of the amine into the acetamido derivative by intramolecular acetyl transfer.
  • 44
    • 77956457157 scopus 로고    scopus 로고
    • note
    • For a detailed description of this assay employed by the same research group in earlier work, see
  • 52
    • 77956494289 scopus 로고    scopus 로고
    • note
    • The structures of these compounds reported in the original paper of Bew et al. are incorrect because the carbohydrate moiety shown is maltose instead of lactose as stated in the text.
  • 65
    • 77956472065 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 74
    • 77956463766 scopus 로고    scopus 로고
    • note
    • The differential functionalization of only one hydroxy group at the lower rim of a calix[4]arene involved monoglycosylation by d -mannofuranose diacetonide via Mitsunobu reaction (see refs 6 and 8) followed by orthogonal protection of the residual hydroxy groups and removal of the sugar residue. Then the free hydroxy group was duly functionalized as required.
  • 80
    • 77956458241 scopus 로고    scopus 로고
    • note
    • For accounts mainly dealing with the work carried out by this group, see
  • 91
    • 77956495380 scopus 로고    scopus 로고
    • note
    • The starting materials for the preparation of compound 122 and 123 were isomeric 5,11,17,23-tetraamino-25,26,27,28-tetrapropoxy-calix[4]arenes rigidified in the cone and 1,3-alternate conformation, respectively.
  • 102
    • 77956467717 scopus 로고    scopus 로고
    • The syntheses of all azido-calix[4]arene derivatives shown in Schemes 31 - 33 were reported in the original papers of refs 43 and 70
    • The syntheses of all azido-calix[4]arene derivatives shown in Schemes 31 - 33 were reported in the original papers of refs 43 and 70.
  • 136
    • 0035532130 scopus 로고    scopus 로고
    • note
    • Aoyama and co-workers reported in a short communication that also a calix[4]resorcarene-based cluster bearing 48 α- d -glucopyranoside units (prepared from octaamine 171 and maltoheptaonolactone) was able to bind double helical DNAs (plasmid pBR322 and calf thymus DNA). See: Hayashida, O., Matsuo, A., and Aoyama, Y. Chem. Lett. 2001, 272.
    • (2001) Chem. Lett. , pp. 272
    • Hayashida, O.1    Matsuo, A.2    Aoyama, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.