78340-47-3

Downstream Products

• 85716-63-8 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-methyl-2-nitro-D-ribo-hex-1-enitol 
• 85716-64-9 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-nitro-α-D-altropyranoside 
• 85747-87-1 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-nitro-β-D-allopyranoside 
• 85747-88-2 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-nitro-α-D-allopyranoside 
• 85716-65-0 methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-nitro-α-D-glucopyranoside 
• 93206-42-9 ethyl 4,6-O-benzylidene-3-cyano-2,3-dideoxy-2-nitro-α-D-allopyranoside 
• 93206-41-8 methyl 4,6-O-benzylidene-3-cyano-2,3-dideoxy-2-nitro-α-D-allopyranoside 
• 78281-21-7 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-3-C-bis<(methoxycarbonyl)methyl>-2-C-nitro-D-ribo-hex-1-enitol 
• 78281-18-2 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-bis<(methoxycarbonyl)methyl>-2-C-nitro-α-D-altropyranoside 
• 78281-18-2 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-bis<(methoxycarbonyl)methyl>-2-C-nitro-α-D-glucopyranoside 
• 78281-15-9 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-(diacethylmethyl)-2-C-nitro-α-D-altropyranoside 
• 78281-15-9 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-(diacethylmethyl)-2-C-nitro-α-D-glucopyranoside 
• 78281-15-9 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-(diacethylmethyl)-2-C-nitro-α-D-mannopyranoside 
• 93206-38-3 methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Synthesis and in vitro activities of a spacer-containing glycophospholipid ligand of a lipopolysaccharide receptor involved in endotoxin tolerance

A glycophospholipid consisting in a derivative of N,N'-acylated and bisphosphorylated 2,3-dideoxy-2,3-diamino-d-glucose, bearing a 6-aminocaproyl side chain as spacer arm at carbon 6 (PPDm2-B), has been synthesized and its effect on murine macrophages evaluated. The synthesis started from 2,3-diamino-d-glucose, which was best obtained from glucosamine essentially by known procedures, since attempts to use another known precursor (3-nitro-glycoside) led to unexpected results. Selective N-acylation was performed with the hydroxysuccinimide ester of (d)-3-benzyloxymyritic acid followed by esterification of the sole primary hydroxyl function by 6-azidocaproylchloride and phosphorylation of the resulting 1,4-diol by treatment with tetrabenzyl pyrophosphate. Hydrogenation on a Pd on carbon catalyst permitted the isolation of 6-(6-aminohexanoyl)-2,3-dideoxy-2,3-di-[(R)-3-hydroxy-tetradecanamido]-α-d-glucopyranose 1,4-diphosphate (PPDm2-B). In mouse macrophages, PPDm2-B enhanced the lipopolysaccharide (LPS)-dependent secretion of tumor necrosis factor alpha (TNF-α), and inhibited the LPS-induced desensitization of these cells. The data suggest that PPDm2-B interacts in a serum-independent way with an LPS receptor different from CD14, and involved in endotoxin tolerance. Binding studies of a fluorescent derivative of PPDm2-B indicated that the expression of this unknown receptor is down-regulated during in vitro culture of the cells. Owing to its spacer arm, PPDm2-B could thus be a promising tool for future studies of this receptor. Copyright (C) 1998 Elsevier Science Ltd.