Myriocin

Base Information

• Chemical Name: Myriocin
• CAS No.: 35891-70-4
• Deprecated CAS: 36564-60-0,37836-36-5
• Molecular Formula: C₂₁H₃₉NO₆
• Molecular Weight: 401.544
• Hs Code.: 29225090
• European Community (EC) Number: 636-862-5
• UNII: YRM4E8R9ST
• DSSTox Substance ID: DTXSID9046360
• Nikkaji Number: J19.020I
• Wikipedia: Myriocin
• Wikidata: Q6948247
• Pharos Ligand ID: SPP6LMF3H76N
• Metabolomics Workbench ID: 67024
• ChEMBL ID: CHEMBL55076
• Mol file: 35891-70-4.mol

Synonyms:2-amino-2-hydroxymethyl-3,4-dihydroxy-14- oxoeicos-6-enoic acid;ISP-1 serine palmitoyltransferase inhibitor;ISP-1 suppressant;myriocin;SPI-1 inhibitor;thermozymocidin

Chemical Property of Myriocin

Chemical Property:

• Vapor Pressure: 6.88E-19mmHg at 25°C
• Melting Point: 170-172℃
• Refractive Index: 1.521
• Boiling Point: 636.7 °C at 760 mmHg
• PKA: 1.79±0.50(Predicted)
• Flash Point: 338.8 °C
• PSA: 141.08000
• Density: 1.123 g/cm³
• LogP: 3.00930
• Storage Temp.: 2-8°C
• Solubility.: methanol: 2 mg/mL
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 18
• Exact Mass: 401.27773796
• Heavy Atom Count: 28
• Complexity: 468

Purity/Quality:

98%,99%, ^*data from raw suppliers

Myriocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O
• Isomeric SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@@](CO)(C(=O)O)N)O)O
• Description: Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus in a murine model.
• Uses: Myriocin is a atypical amino acid and an antibiotic with potent immunosuppressant activity. Studies suggest that the immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction. Myriocin very potent inhibitor of serine palmitoyltransferase and thus blocks the synthesis ceramide, a precursor in sphingomyelin and glycosphingolipid biosynthesis. As a result Myriocin i s a useful biochemical research tool for depleting cells of sphingolipids. Myriocin is an α-amino fatty acid derived from several genera of fungi, notably Myriococcum, Melanconis and Isaria. Myriocin potently inhibits sphingosine biosynthesis by blocking the first enzyme in the pathway, serine palmitoyltransferase. Myriocin induces apoptosis by depleting cellular sphingolipids, inhibits proliferation of IL-2-dependent mouse cytotoxic cells and is a potent immunosuppressant. Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus in a murine model.[Cayman Chemical]

Technology Process of Myriocin

There total 35 articles about Myriocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

(2R,3R,4S)-4-acetamido-4-(acetoxymethyl)-5-oxo-2-[(E)-10-oxohexadec-2-en-1-yl]tetrahydrofuran-3-yl acetate (37818-01-2) → myriocin (35891-70-4,37836-36-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 80 ℃; for 2h;

DOI:10.1016/j.tet.2016.12.066

Reference yield: 84.0%

(1S,5R,6R)-1-hydroxymethyl-6-[(E)-10-oxohexadec-2-en-1-yl]-2-aza-4,7-dioxabicyclo[3.3.0]octane-3,8-dione (475291-29-3) → myriocin (35891-70-4,37836-36-5)

Guidance literature:

With water; sodium hydroxide; In methanol; at 80 ℃; for 2h;

DOI:10.1021/acs.orglett.9b01778

Reference yield: 80.0%

N-benzoylanhydromyriocin (158356-12-8) → myriocin (35891-70-4,37836-36-5)

Guidance literature:

With sodium hydroxide;

DOI:10.1248/cpb.42.994

upstream raw materials:

2-benzoylamino-2-benzoyloxymethyl-2,5-dideoxy-3-O-benzoyl-5-(E)-9-oxopentadec-1-enyl-D-lyxono-1,4-lactone

N-benzoylanhydromyriocin

(2R,3R,4S)-4-acetamido-4-(acetoxymethyl)-5-oxo-2-[(E)-10-oxohexadec-2-en-1-yl]tetrahydrofuran-3-yl acetate

(1S,5R,6R)-1-hydroxymethyl-6-[(E)-10-oxohexadec-2-en-1-yl]-2-aza-4,7-dioxabicyclo[3.3.0]octane-3,8-dione

Downstream raw materials:

5-benzoylamino-5-benzoyloxymethyl-2,5-dideoxy-4-O-benzoyl-D-mannurono-3,6-lactone

(3S,4R,5R)-3-Amino-4-hydroxy-3-hydroxymethyl-5-((E)-10-oxo-hexadec-2-enyl)-dihydro-furan-2-one

mycestericin B

2-benzoylamino-2-benzoyloxymethyl-2,5-dideoxy-3-O-benzoyl-5-(E)-9-oxopentadec-1-enyl-D-lyxono-1,4-lactone

Refernces

• 1、 Noda, Narumi,Nambu, Hisanori,Ubukata, Kana,Fujiwara, Tomoya,Tsuge, Kiyoshi,Yakura, Takayuki. "Total synthesis of myriocin and mycestericin D employing Rh(II)-catalyzed C[sbnd]H amination followed by stereoselective alkylation". . p. 868 - 878. Retrieved 2017/01/28.
• 2、 Oishi, Takeshi,Ando, Koji,Inomiya, Kenjin,Sato, Hideyuki,Iida, Masatoshi,Chida, Noritaka. "Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction". . p. 1927 - 1947. Retrieved 2007/10/03.