18944-28-0

Basic information

• Product Name: 3-KETO-DIHYDROSPHINGOSINE HCL
• Synonyms: 3-KETO-DIHYDROSPHINGOSINE HCL;3-KETO-SPHINGANINE HYDROCHLORIDE;3-KETO-DIHYDROSPHINGOSINE HYDROCHLORIDE;3-keto-Dihydrosphingosine.HCl NEW
• CAS NO: 18944-28-0
• Molecular Formula: C18H37NO2.ClH
• Molecular Weight: 335.956
• Mol File: 18944-28-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-KETO-DIHYDROSPHINGOSINE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-KETO-DIHYDROSPHINGOSINE HCL(18944-28-0)
• EPA Substance Registry System: 3-KETO-DIHYDROSPHINGOSINE HCL(18944-28-0)

Safety Data

• Hazardous Substances Data: 18944-28-0(Hazardous Substances Data)

Usage

Uses

3-Ketodihydrosphingosine is derived from N-Boc-L-Serine (B667355), which is an N-Boc-protected form of L-Serine (S270975). L-Serine is a non-essential amino acid that is required for the synthesis of sphinogolipids and phosphatidylserine, compounds that are important for central nervous system neuronal survival. L-Serine is also important in intermediary metabolism in eukaryotic cells.

Upstream product

• 437609-37-5 (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one 

Downstream Products

• 111149-09-8 N-palmitoyl-D-ribo-phytosphingosine 
• 21275-74-1 dihydroceramide 
• 554-62-1 D-ribo-phytosphingosine 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 

Relevant articles and documents

Simplifungin and Valsafungins, Antifungal Antibiotics of Fungal Origin

The targets of antifungal antibiotics in clinical use are more limited than those of antibacterial antibiotics. Therefore, new antifungal antibiotics with different mechanisms of action are desired. In the course of our screening for antifungal antibiotics of microbial origins, new antifungal antibiotics, simplifungin (1) and valsafungins A (2) and B (3), were isolated from cultures of the fungal strains Simplicillium minatense FKI-4981 and Valsaceae sp. FKH-53, respectively. The structures of 1 to 3 including their absolute stereochemistries were elucidated using various spectral analyses including NMR and collision-induced dissociation (CID)-MS/MS as well as chemical approaches including modifications to the Mosher's method. They were structurally related to myriocin. They inhibited the growth of yeast-like and zygomycetous fungi with MICs ranging between 0.125 and 8.0 μg/mL. An examination of their mechanisms of action by the newly established assay using LC-MS revealed that 1 and 2 inhibited serine palmitoyltransferase activity, which is involved in sphingolipid biosynthesis, with IC50 values of 224 and 24 nM, respectively.