Strictosidine

Base Information

• Chemical Name: Strictosidine
• CAS No.: 20824-29-7
• Molecular Formula: C₂₇H₃₄N₂O₉
• Molecular Weight: 530.575
• UNII: 45T874R5N4
• DSSTox Substance ID: DTXSID40943068
• Nikkaji Number: J15.956E
• Wikipedia: Strictosidine
• Wikidata: Q2356148
• Metabolomics Workbench ID: 50958
• ChEMBL ID: CHEMBL402211
• Mol file: 20824-29-7.mol

Synonyms:isovincoside;strictosidine;strictosidine, (2S-(2alpha,3beta,4beta(S*)))-isomer

Chemical Property of Strictosidine

Chemical Property:

• Vapor Pressure: 1.78E-24mmHg at 25°C
• Melting Point: 161-165 °C
• Boiling Point: 763°Cat760mmHg
• PKA: 12.81±0.70(Predicted)
• Flash Point: 415.3°C
• PSA: 162.73000
• Density: 1.44g/cm³
• LogP: 0.72170
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 530.22643067
• Heavy Atom Count: 38
• Complexity: 887

Purity/Quality:

98% ^*data from raw suppliers

Strictosidine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(C(C1CC2C3=C(CCN2)C4=CC=CC=C4N3)C=C)OC5C(C(C(C(O5)CO)O)O)O
• Isomeric SMILES: COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• General Description: Strictosidine is a key intermediate in the biosynthesis of quinine, serving as a precursor that is enzymatically converted into dihydrocorynantheal via reduction and decarboxylation by the enzymes CpDCS and CpDCE, respectively, in the early steps of the pathway.

Technology Process of Strictosidine

There total 25 articles about Strictosidine 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: 84.0%

tryptamine (61-54-1) + secologanin (19351-63-4) → strictosidine (19456-89-4,20824-29-7)

Guidance literature:

In aq. phosphate buffer; at 5 ℃; Enzymatic reaction;

Reference yield: 35.2%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-carboxystrictosidine → strictosidine (19456-89-4,20824-29-7) + dolichantoside (68727-52-6)

Guidance literature:

DOI:10.1248/cpb.45.1231

Reference yield: 27.0%

secologanin (19351-63-4) + tryptamine hydochloride (343-94-2) → strictosamide (22621-94-9,23141-27-7,23141-25-5) + strictosidine (19456-89-4,20824-29-7) + 3β(R)-vincosamide (23141-27-7,22621-94-9,23141-25-5)

Guidance literature:

With tryptamine; acetic acid; In water; at 100 ℃; for 6h;

DOI:10.1021/np990150r

upstream raw materials:

tryptamine

secologanin

(4S)-6t-[tetrakis-O-(2,2,2-trichloro-ethoxycarbonyl)-β-D-glucopyranosyloxy]-4r-[(S)-2-(2,2,2-trichloro-ethoxycarbonyl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl]-5c-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

diazomethane

Downstream raw materials:

cathenamine

epicathenamine

strictosidine aglycone

16(R),19(Z)-isositsirikine

Refernces

Early and Late Steps of Quinine Biosynthesis

10.1021/acs.orglett.1c00206

The study investigates the enzymatic basis for quinine biosynthesis, focusing on the early and late steps of the pathway. Quinine, an alkaloid produced by Cinchona trees, is historically used as an antimalarial drug and as a flavor ingredient in beverages. The researchers combined metabolomics and transcriptomics data from different tissues of Cinchona pubescens to identify genes involved in quinine biosynthesis. They discovered three key enzymes: a medium-chain alcohol dehydrogenase (CpDCS), an esterase (CpDCE), and an O-methyltransferase (CpOMT1). CpDCS and CpDCE were involved in converting strictosidine aglycone to dihydrocorynantheal, an intermediate in quinine biosynthesis, through reduction and esterase-triggered decarboxylation. CpOMT1 was found to specifically act on 6′-hydroxycinchoninone, suggesting a preferred order for the late steps of quinine biosynthesis. The chemicals used in the study included strictosidine, corynantheine aldehyde, dihydrocorynantheine aldehyde, and cinchoninone, among others, which served as substrates, intermediates, and products in the biosynthetic pathway of quinine. The purpose of these chemicals was to elucidate the enzymatic steps and intermediates involved in the biosynthesis of quinine, providing insights into the metabolic pathways and potential for synthetic biology applications in quinine production.

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