메뉴 건너뛰기




Volumn 14, Issue 4, 2006, Pages 1182-1188

C-Glycoside analogues of β-galactosylceramide with a simple ceramide substitute: Synthesis and binding to HIV-1 gp120

Author keywords

Aza C glycoside gp120; C Glycoside; Galactosyl ceramide; Oxocarbenium ion

Indexed keywords

1,5 ANHYDRO 1 C HEPTADECYL DEXTRO GALACTITOL; 1,5 DIDEOXY 1 C HEPTADECYL 1,5 IMINO DEXTRO GALACTITOL; BETA GALACTOSIDE; CARBOHYDRATE; GALACTOSYLCERAMIDE; GLYCOLIPID; GLYCOPROTEIN GP 120; GLYCOSIDE; STEARIC ACID; THIOACETALDEHYDE; UNCLASSIFIED DRUG;

EID: 30344434993     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.044     Document Type: Article
Times cited : (26)

References (37)
  • 24
    • 0034697244 scopus 로고    scopus 로고
    • Alcohol 7 is available in five steps from commercially available d-lyxose in an overall yield of approximately 60%. N. Khan, X. Cheng, and D.R. Mootoo J. Org. Chem. 65 2000 2544 2547
    • (2000) J. Org. Chem. , vol.65 , pp. 2544-2547
    • Khan, N.1    Cheng, X.2    Mootoo, D.R.3
  • 25
    • 0033583130 scopus 로고    scopus 로고
    • For related examples of stereoselective hydroboration of Cl-substituted galactals: D. Calimente, and M.H.D. Postema J. Org. Chem. 64 1999 1770 1771
    • (1999) J. Org. Chem. , vol.64 , pp. 1770-1771
    • Calimente, D.1    Postema, M.H.D.2
  • 35
    • 18844471722 scopus 로고    scopus 로고
    • An aromatic Phe residue in the V3 loop of HIV-1 gp120 is directly involved in GalCer binding, so that the aromatic phenyl cycle stacks onto the sugar cycle. N. Taieb, N. Yahi, and J. Fantini Adv. Drug Deliv. Rev. 56 2004 779 794 An interesting speculation is that the protonated azasugar analogue could engage in a favorable NH-π interaction with the aromatic ring, leading to increased binding of 4 to gp120 (relative to 1 and 3). Alternatively, it is conceivable that the electrostatic repulsion between the protonated amine in adjacent molecules of 4 could reduce the overall lipid-lipid attraction in monolayers formed from 4 relative to monolayers from the neutral analogues 1 and 3. This effect could lead to a monolayer of 4 that is intrinsically more 'penetrable' (i.e., with a greater critical pressure of insertion)
    • (2004) Adv. Drug Deliv. Rev. , vol.56 , pp. 779-794
    • Taieb, N.1    Yahi, N.2    Fantini, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.