Leurosine, sulfate

Base Information

• Chemical Name: Leurosine, sulfate
• CAS No.: 23360-92-1
• Molecular Formula: C46H56N4O9
• Molecular Weight: 808.972
• NSC Number: 528004,328898,90636
• Mol file: 23360-92-1.mol

Synonyms:Leurosine, sulfate;NSC90636;NSC528004;54081-68-4;Viinleurosine sulfate;SCHEMBL10684121;NSC328898;AKOS030242409;NSC-328898;CATHARANTHUS ROSEUS ALKALOID B99752 K295

Chemical Property of Leurosine, sulfate

Chemical Property:

• Melting Point: 202-205℃
• Refractive Index: 1.677
• PKA: 11.36±0.60(Predicted)
• PSA: 146.40000
• Density: 1.39 g/cm³
• LogP: 4.29570
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 906.37210909
• Heavy Atom Count: 64
• Complexity: 1830

Purity/Quality:

95%-98% ^*data from raw suppliers

Vinleurosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CN3CCC4=C(C(CC(C3)C1O2)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41.OS(=O)(=O)O
• Isomeric SMILES: CC[C@]12CN3CCC4=C([C@](C[C@H](C3)[C@H]1O2)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41.OS(=O)(=O)O
• Description: Vinqa rosea yields this complex dimeric alkaloid which forms colourless crystals that are best purified by recrystallization from acetonitrile. It crystallizes with 8 moles of H20 and loses solvent when heated at In-5°C. It is also dextro? rotatory with [α]26D + n° (CHCI3)’ A crystalline SUlphate is known which has m.p. 238-242°C (dec.) and [α]D - 8.3° (MeOH). The N(b)-oxide is identical with pleurosine (q.v.).
• Uses: Vinleurosine is an antitumor compound derived from Vinca Rosea. Antineoplastic.

Technology Process of Leurosine, sulfate

There total 5 articles about Leurosine, sulfate 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: 8.3%

anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4) → catharine (1355-31-3) + vinblastine + vinamidine + (15'R)-hydroxyvinamidine + vinleurosine (23360-92-1)

Guidance literature:

With sodium tetrahydroborate; flavin adenine dinucleotide; manganese(ll) chloride; Product distribution; Multistep reaction; biotransformation of 3',4'-anhydrovinblastine by C_. roseus cultures (cell line AC₃) in 1-B₅ medium;

Reference yield:

anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4) → Vincristine (57-22-7) + catharine + vinblastin (363623-08-9,906333-70-8) + vinleurosine (23360-92-1)

Guidance literature:

With cell-free extracts from Catharanthus roseus; Product distribution; Mechanism; Ambient temperature; biosynthesis of the products were studied; experiment was performed with 3',4'-anhydrovinblastine and the incorporation of the radiolabel into the products were investigated;

DOI:10.1002/hlca.19820650716

Reference yield:

vindoline (2182-14-1) + 18(R)-methoxycarbonylcleavamine (26251-91-2) → anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4) + vinblastin (363623-08-9,906333-70-8) + vinleurosine (23360-92-1)

Guidance literature:

With Flavin mononucleotide; manganese(ll) chloride; In water; at 25 ℃; pH=7; Tris-HCl buffer; near-ultraviolet light irradiation;

DOI:10.1271/bbb.90545

upstream raw materials:

anhydrovinblastine

catharinthine

vindoline

18(R)-methoxycarbonylcleavamine

Downstream raw materials:

22-Oxoleurosin

pleurosine

anhydrovinblastine

Refernces

• 1、 Kutney, James Peter,Botta, Bruno,Boulet, Camille Andre,Buschi, Carlos Alberto,Choi, Lewis Siu Leung,et al.. "ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XVI. BIOTRANSFORMATION OF 3',4'-ANHYDROVINBLASTINE WITH CATHARANTHUS ROSEUS CELL CULTURES AND ENZYME SYSTEMS". . p. 629 - 638. Retrieved 2007/10/02.
• 2、 Kutney, James Peter,Boulet, Camille Andre,Choi, Lewis Siu Leung,Gustowski, Wlodzimierz,McHugh, Michael,et al.. "ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XIV. THE ROLE OF UNSTABLE DIHYDROPYRIDINIUM INTERMEDIATES IN THE BIOSYNTHESIS OF BISINDOLE ALKALOIDS". . p. 613 - 620. Retrieved 2007/10/02.