2005
DOI: 10.1002/ejoc.200500053
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Immunomodulatory α‐Galactoglycosphingolipids: Synthesis of 2'‐Fluoro‐2'‐deoxy‐α‐galactosylceramide and an Evaluation of Its Immunostimulating Properties

Abstract: In the framework of a project to assess the immunomodulating properties of α‐galactosyl glycosphingolipids, the total synthesis of 1‐O‐(2‐fluoro‐2‐deoxy‐α‐D‐galactopyranosyl)‐2‐docosanoylamino‐1,3,4‐octadecanetriol (1), a 2'‐fluoro analogue of the immunostimulating α‐galactoglycosphingolipids, was accomplished. The glycosidation reaction of the azido precursor of sphingosine was performed using the Mukaiyama glycosidation reaction. The stimulation of mouse splenocyte proliferation by the 2'‐fluoro analogue was… Show more

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Cited by 33 publications
(21 citation statements)
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“…A similar situation was encountered in the activation of 2-fluoroglycosyl donors. [226] Moderate to good b selectivities were also observed in the glycosylation of a range of acceptors with rhamnosyl donors protected with sulfonyl groups at the 2-O-position, as exemplified in Scheme 21 b by the reaction of 148.…”
Section: Neighboring Protecting Groups That Promote the Formation Of mentioning
confidence: 88%
“…A similar situation was encountered in the activation of 2-fluoroglycosyl donors. [226] Moderate to good b selectivities were also observed in the glycosylation of a range of acceptors with rhamnosyl donors protected with sulfonyl groups at the 2-O-position, as exemplified in Scheme 21 b by the reaction of 148.…”
Section: Neighboring Protecting Groups That Promote the Formation Of mentioning
confidence: 88%
“…5 The equatorial C2–OH group of the galactose was also found to be crucial for the activity of α-GalCer; any modification at this position largely abolished activity. 6 Modifications at the C3- and C6–OH groups of the galactose was found to be tolerated. 7 The structure–activity relationship (SAR) studies centered on the ceramide moiety of α-GalCer may be grouped into modifications of the acyl and phytosphingosine chains, and of the polar portion of the ceramide.…”
mentioning
confidence: 99%
“…[22][23][24] Therefore, the former three hydroxy groups seem to play important roles in making a stable CD1d-antigen-TCR complex and hence show the potent immunostimulatory activities. Indeed, many analogs have been developed by modification of the three former hydroxy groups to other functional groups, for example, H (deoxy), F, N 3 , NH 2 , NHAc, OMe, and O(CH 2 ) 2 OH, 46,[104][105][106][107][108][109] but none of these analogs showed potent bioactivities, except for the 3-O-sulfo--galactosyl analog of 1 (37, Fig. 6), 105,110,111) and the 4-O-phenylpropyl--galactosyl analog (Ar3-GSL, 38).…”
Section: Modification Of the Sugar Part Of Krn7000mentioning
confidence: 99%