2S3Rsphinganine

2S3Rsphinganine, also known as dihydrosphingosine or (2S,3R)-dihydrosphingosine, is a long-chain saturated sphingoid base and the dihydro analogue of sphingosine. It is a fundamental component of sphingolipids and provides the core scaffold for more complex molecules such as ceramides and glycosphingolipids.

Chemically, 2S3Rsphinganine is an 18-carbon aliphatic amino alcohol bearing a primary hydroxyl group at carbon 1, a secondary hydroxyl group at carbon 3, and an amino group at carbon 2. Its stereochemistry is defined as 2S and 3R, which corresponds to the naturally occurring configuration found in most organisms. The molecule is saturated, meaning it lacks the trans-double bond present in sphingosine.

Biologically, sphinganine arises in the de novo synthesis of sphingolipids. The pathway begins with the condensation of serine and palmitoyl-CoA to form 3-ketosphinganine, which is reduced to sphinganine. Sphinganine can be N-acylated to form dihydroceramide and then desaturated to ceramide. The 2S,3R stereoisomer is the predominant natural form of this sphingoid base in many tissues.

Functionally, 2S3Rsphinganine serves as a key precursor to a broad family of sphingolipids that participate in membrane structure and cellular signaling. Alterations in sphingolipid metabolism involving dihydrosphingosine can be associated with metabolic disorders and stress responses. In research and analytical contexts, 2S3Rsphinganine is used as a standard or reference compound for studying sphingolipid metabolism and lipidomics.