3sulfate

3sulfate is a descriptive term used in chemistry to denote a sulfate group, –SO4, that is attached at the third position of a molecule. It is not a single defined compound, but a shorthand encountered in organic and biochemistry to indicate regioselective sulfation at position 3 of a substrate, such as a sugar, steroid framework, or other carbon skeleton.

In carbohydrate chemistry, 3-sulfation refers to introducing a sulfate ester at the C-3 carbon of a sugar unit. This pattern of sulfation contributes to the overall charge and conformation of the molecule and can influence interactions with proteins and other carbohydrates. In biology, sulfotransferase enzymes mediate regioselective sulfation, including at the 3-position, which can affect molecular recognition, binding affinity, and biological activity.

Synthesis and occurrence: 3sulfate-containing structures can arise enzymatically in vivo through sulfotransferase activity or be prepared chemically using sulfating reagents such as sulfur trioxide-pyridine complexes under controlled conditions. 3-sulfate esters are generally stable under neutral to mildly basic conditions but can hydrolyze under strong acidic or basic conditions, depending on the substrate and protecting groups used in synthesis.

Properties and detection: sulfate esters carry a negative charge at physiological pH and are highly polar, increasing water solubility. In analytical contexts, 3sulfate motifs are detected by techniques such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry, with characteristic fragmentation patterns for sulfate esters in MS.

See also: sulfate, sulfation, sulfate ester, glycosaminoglycans.