Lyngbyatoxin a

Base Information

• Chemical Name: Lyngbyatoxin a
• CAS No.: 70497-14-2
• Deprecated CAS: 56645-57-9
• Molecular Formula: C₂₇H₃₉N₃O₂
• Molecular Weight: 437.626
• UNII: SE69L721CS
• DSSTox Substance ID: DTXSID90880015
• Nikkaji Number: J147.589D
• Wikipedia: Lyngbyatoxin-a
• Wikidata: Q5934205
• Metabolomics Workbench ID: 98903
• ChEMBL ID: CHEMBL5172923
• Mol file: 70497-14-2.mol

Synonyms:lyngbyatoxin A;teleocidin A;teleocidin A 1;teleocidin A-1;teleocidin A1

Chemical Property of Lyngbyatoxin a

Chemical Property:

• Vapor Pressure: 1.36E-18mmHg at 25°C
• Boiling Point: 665.1 °C at 760 mmHg
• PKA: 14.39±0.10(Predicted)
• Flash Point: 356 °C
• PSA: 68.36000
• Density: 1.06 g/cm³
• LogP: 5.24580
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 437.30422750
• Heavy Atom Count: 32
• Complexity: 701

Purity/Quality:

99% ^*data from raw suppliers

Lyngbyatoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: other linear peptide (Lyngbya toxin (alkaloid))
• Canonical SMILES: CC(C)C1C(=O)NC(CC2=CNC3=C(C=CC(=C23)N1C)C(C)(CCC=C(C)C)C=C)CO
• Isomeric SMILES: CC(C)[C@H]1C(=O)N[C@@H](CC2=CNC3=C(C=CC(=C23)N1C)[C@](C)(CCC=C(C)C)C=C)CO
• Uses: LYNGBYATOXIN A is a potent nematocide and acaricide produced by Streptoverticillium strains, first reported in 1960. LYNGBYATOXIN A is a potent activator of protein kinase C, and also a tumour promoting agent and inducer of colony-stimulating factors. More recently, LYNGBYATOXIN A has been shown to regulate the expression of several genes. To date, the lack of availability of teleocidin has meant the truncated teleocidin-like (-)indolactam has been used to mimic teleocidin cellular responses. Teleocidin A is a potent nematocide and acaricide produced by Streptoverticillium strains, first reported in 1960. Teleocidin A is a potent activator of protein kinase C, and also a tumor promoting agent and inducer of colony-stimulating factors. More recently, teleocidin A1 has been shown to regulate the expression of several genes. To date, the lack of availability of teleocidin has meant the truncated teleocidin-like (-)indolactam has been used to mimic teleocidin cellular responses. Lyngbyatoxin is a cyanotoxin produced by cyanobacteria Anabaena sp.

Technology Process of Lyngbyatoxin a

There total 22 articles about Lyngbyatoxin a 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: 63.0%

C33H53N3O2Si (1638769-41-1) → Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With lithium tetrafluoroborate; camphor-10-sulfonic acid; In tetrahydrofuran; at 23 ℃;

DOI:10.1039/c4sc00256c

Reference yield: 4.0%

(S)-2-{[3-(2-Amino-3-hydroxy-propyl)-7-((R)-1,5-dimethyl-1-vinyl-hex-4-enyl)-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid → (+)-Teleocicin A-2 (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + (10S,13R)-5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; 0 deg C, 1 h, then room temp. 24 h;

DOI:10.1016/S0040-4039(00)96097-0

Reference yield: 4.0%

(S)-2-{[3-(2-Amino-3-hydroxy-propyl)-7-((R)-1,5-dimethyl-1-vinyl-hex-4-enyl)-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid → (+)-Teleocicin A-2 (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + (10S,13R)-5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; 0 deg C, 1 h, then room temp. 24 h;

DOI:10.1016/S0040-4039(00)96097-0

upstream raw materials:

N-methyl-L-valyl-L-tryptophanol

(-)-7-bromo-14-O-TBDMS-indolactam-V

C₃₆H₅₈N₄O₄Si

C₃₂H₅₁N₃O₃Si

Downstream raw materials:

21,22-dihydroteleocidin A-2

21,22-dihydroteleocidin A-1

teleocidin B-4

des-O-methyl-olivoretin C

Refernces

• 1、 Huynh, Minh U.,Elston, Matthew C.,Hernandez, Nick M.,Ball, David B.,Kajiyama, Shin-Ichiro,Irie, Kazuhiro,Gerwick, William H.,Edwards, Daniel J.. "Enzymatic production of (-)-indolactam V by LtxB, a cytochrome P450 monooxygenase". experimental part. p. 71 - 74. Retrieved 2010/04/28.
• 2、 Muratake, Hideaki,Natsume, Mitsutaka. "TOTAL SYNTHESIS OF LYNGBYATOXIN A (TELEOCIDIN A-1) AND TELEOCIDIN A-2". . p. 2265 - 2268. Retrieved 2007/10/02.