Pseurotin A

Base Information

• Chemical Name: Pseurotin A
• CAS No.: 58523-30-1
• Molecular Formula: C22H25 N O8
• Molecular Weight: 431.442
• UNII: H73C5W8FNE
• DSSTox Substance ID: DTXSID901017601
• Wikipedia: Pseurotin_A
• Wikidata: Q15424789
• Metabolomics Workbench ID: 63428
• ChEMBL ID: CHEMBL253179
• Mol file: 58523-30-1.mol

Synonyms:pseurotin;pseurotin A

Chemical Property of Pseurotin A

Chemical Property:

• Vapor Pressure: 1E-23mmHg at 25°C
• Melting Point: 126.0-126.9℃
• Boiling Point: 751.5°C at 760 mmHg
• PKA: 14.76±0.20(Predicted)
• Flash Point: 408.3°C
• PSA: 142.39000
• Density: 1.41g/cm³
• LogP: 0.33160
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (10 mg/ml)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 431.15801676
• Heavy Atom Count: 31
• Complexity: 814

Purity/Quality:

99% ^*data from raw suppliers

PB1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC(C(C1=C(C(=O)C2(O1)C(C(NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O
• Isomeric SMILES: CC/C=C\[C@@H]([C@@H](C1=C(C(=O)[C@@]2(O1)[C@H]([C@@](NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O
• General Description: Pseurotin is a bioactive natural product derived from *Aspergillus fumigatus*, characterized by a complex spiro-ring core structure and notable chemical diversity. Its biosynthesis involves key enzymatic steps, including the action of PsoF, a bifunctional protein that mediates C-methylation and epoxide formation, contributing to the structural variations observed within the pseurotin family. pseurotin and its derivatives, such as pseurotin A, exhibit significant bioactivity, though the specific biological roles or applications are not detailed in the provided abstract.

Technology Process of Pseurotin A

There total 42 articles about Pseurotin 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: 67.0%

methanol (67-56-1) + (5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (562858-39-3) → pseurotin A (58523-30-1) + (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (149883-42-1)

Guidance literature:

With acetyl chloride; In methanol; at 20 ℃; for 11h;

DOI:10.1021/ol034630s

Reference yield: 54.0%

(+)-synerazol (127941-81-5) → pseurotin A (58523-30-1)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 30 ℃; for 24h;

DOI:10.7164/antibiotics.57.537

Reference yield: 41.0%

methanol (67-56-1) + (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (149883-42-1) → pseurotin A (58523-30-1)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 40 ℃;

DOI:10.3987/com-03-s(p)25

upstream raw materials:

(12S,13S)-12,13-dibromo-12,13-dihydropseurotin A

methanol

(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

(5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Downstream raw materials:

trans-2-pentenal

C₂₄H₂₉NO₈

C₂₁H₂₃NO₈

C₂₂H₂₅NO₈

Refernces

Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase: Generation of chemical diversity

10.1002/anie.201404804

The study primarily focuses on elucidating the biosynthetic pathway of pseurotins, a family of structurally related Aspergillal natural products with significant bioactivity. Researchers systematically deleted pseurotin biosynthetic genes in Aspergillus fumigatus and characterized tailoring enzymes in vivo and in vitro to determine biosynthetic intermediates and the genes responsible for their formation. Key chemicals used in the study include azaspirene, the predominant precursor, and pseurotin A, a compound of interest. The study also identified PsoF, a bifunctional fusion protein consisting of a C-methyltransferase and an FAD-containing monooxygenase domain, which plays a crucial role in the methylation of the polyketide backbone and the formation of the epoxide group in pseurotins. Other chemicals mentioned include N-acetylcysteamine (NAC) thioester, used as a mimic for the natural substrate in the C-methylation step, and various pseurotin-type compounds and their intermediates, which were analyzed for their roles in the biosynthetic pathway. The purpose of using these chemicals was to understand the combinatorial nature of pseurotin biosynthesis, the formation of the spiro-ring core structure, and the generation of chemical diversity within the pseurotin family of compounds.

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