Myriocin

Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is a non-proteinogenic amino acid derived from certain thermophilic fungi.

Myriocin
Names
Preferred IUPAC name
(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)icos-6-enoic acid
Other names
Antibiotic ISP-1; Thermozymocidin
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
5113331
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.620
KEGG
PubChem CID
RTECS number
  • JX3890000
UNII
UN number 2811
InChI
  • InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28) N
    Key: ZZIKIHCNFWXKDY-UHFFFAOYSA-N N
  • InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
  • InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
    Key: ZZIKIHCNFWXKDY-GNTQXERDSA-N
SMILES
  • CCCCCCC(=O)CCCCCCC=CCC(O)C(O)C(N)(CO)C(O)=O
  • O=C(O)[C@@](N)([C@@H](O)[C@H](O)C/C=C/CCCCCCC(=O)CCCCCC)CO
Properties
Chemical formula
C21H39NO6
Molar mass 401.54 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis.[1] 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

  1. 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.
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