A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides

Abstract

Disaccharide units containing a latent aldehyde surrogate at O4 provide late-stage access to terminal aldehyde LMWH and HS deca and dodecasaccharides.

Revealing biomedically relevant cell and lectin type-dependent structure–activity profiles for glycoclusters by using tissue sections as an assay platform

“…The synthesis of compound 4, using conjugation sites on d -mannitol to implement tetravalency, started with 13 and is summarised in Scheme 2 . 32 Tetrapropargylation was followed by removal of the acetonide group, resulting in 14. Next, CuAAC with 12 and subsequent deacetylation generated 4.…”

Developments in the Chemical Synthesis of Heparin and Heparan Sulfate

“…Gardiner's group also described installation of a non-reducing O4 handle in order to introduce conjugation-suitable, terminal functionality to biologically important HS oligosaccharides (Figure 2). [39] Their approach introduced a d-GlcN O4aldehyde-level bearing unit (using an appropriate disaccharide donor) to remain latent throughout oligosaccharide synthesis. This latent aldehyde tag (LAT) was set to be unmasked at the final stage of synthesis, yielding fully sulfated, heparin-type This compared to an earlier, reducing end LAT unit introduced by the group to enable radiolabelled HS dodecasaccharide synthesis.…”

Glycerol mycolates from synthetic mycolic acids

“…The mixture was stirred for 1 h then R-tosylate (2) (40 mg, 0.13 mmol) was added .The mixture was brought to 70 °C and left at this temperature for 18 h, then worked up and purified as before to give a semi-solid, compound (12d) (64 mg, 85%), ሾ ߙሿ ଶସ − 8. 14) [37], and acid in dry DMF:THF (1:5, 2 mL) at room temperature. The mixture was stirred at 70 ºC for 2 days, then diluted with ethyl acetate (10 mL) and water (10 mL).…”