Myriocin

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Myriocin
Myriocin
Identifiers
CAS number 35891-70-4 N
PubChem 6438394 (6EYesY, 301119 () YesY
ChemSpider 4942874 (2S,3R,4R,6E) YesY, 11654743 (6EYesY, 266093 () YesY, 21467337 (3S,4S,6EYesY
UN number 2811
KEGG C19914 N
ChEBI CHEBI:183131 N
ChEMBL CHEMBL55076 YesY
RTECS number JX3890000
Beilstein Reference 5113331
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C21H39NO6
Molar mass 401.54 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is an atypical amino acid and an antibiotic derived from certain thermophilic fungi. Among the producing strains are Mycelia sterilia[1] and Isaria sinclairii.

Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis.[2] Due to this property, it is used in biochemical research as a tool for depleting cells of sphingolipids.

Myriocin was shown to inhibit the proliferation of an IL-2-dependent mouse cytotoxic T cell line.

Myriocin possesses immunosuppressant activity. It is reported to be 10 to 100 fold more potent than ciclosporin.

The multiple sclerosis drug fingolimod was derived from myriocin by using structure–activity relationship studies to determine the parts of the molecule important to its activity.

References[edit]

  1. ^ Myriocin from Fermentek
  2. ^ Miyake Y, Kozutsumi Y, Nakamura S, Fujita T, Kawasaki T (1995). "Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin". Biochem. Biophys. Res. Commun. 211 (2): 396–403. doi:10.1006/bbrc.1995.1827. PMID 7794249.