Validamycin A

Base Information

• Chemical Name: Validamycin A
• CAS No.: 37248-47-8
• Molecular Formula: C20H35NO13
• Molecular Weight: 497.497
• European Community (EC) Number: 609-372-4
• UNII: 313E9620QS
• DSSTox Substance ID: DTXSID4058073
• Nikkaji Number: J108.001F
• Wikipedia: Validamycin
• Metabolomics Workbench ID: 69803
• ChEMBL ID: CHEMBL1923413
• Mol file: 37248-47-8.mol

Synonyms:jinggangmycin;Validacin;validamycin A

Chemical Property of Validamycin A

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 130-135 °C
• Refractive Index: 1.689
• Boiling Point: 813.7 °C at 760 mmHg
• PKA: 6.0(at 25℃)
• Flash Point: 445.9 °C
• PSA: 253.02000
• Density: 1.69 g/cm³
• LogP: -6.36180
• Storage Temp.: 0-6°C
• Water Solubility.: Readily soluble
• XLogP3: -6.3
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 497.21084017
• Heavy Atom Count: 34
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Validamycin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1C(C(C(C(C1NC2C=C(C(C(C2O)O)O)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N[C@H]2C=C([C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
• Description: Validamycin A is produced by the fermentation of Streptomyces hygroscopicus var. limoneus nov. var (30). Structure revised (31). Colorless, odorless, hygroscopic powder. V.p. Negligible at room temperature. Solubility: Readily soluble in water, soluble in methanol, dimethylformamide and dimethyl sulfoxide. Slightly soluble in ethanol and acetone. Sparingly soluble in diethyl ether and ethyl acetate. pKa 6.0 Stability [α]24D + 110? (water).
• Uses: Validamycin A (>70%) Hydrochloride Salt is a metabolite of Validamycin A (>70%) (V943430) which is an antibiotic fungicide that inhibits trehalase activity in plants, insects, and fungi. Validamycin A is the major analogue of a family of cyclitol disaccharides isolated from Streptomyces hygroscopicus var. limoneus by researchers at Takeda in 1970. Although commonly regarded as an aminoglycoside, validamycin shares little in common with conventional aminoglycosides such as streptomycin and gentamicin. Validamycin A is a potent antifungal agent and is used to control fungi in crop production. Validamycin A acts as a potent inhibitor of trehalase, an important enzyme in carbohydrate storage and ultilisation in fungi. Validamycin A is used for the control of Rhizoctonia diseases in rice (sheath blight), potatoes, vegetables, strawberries, tobacco and other crops.

Technology Process of Validamycin A

There total 20 articles about Validamycin 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:

D-Glucose (2280-44-6) → validamine (32780-32-8) + valienamine (38231-86-6) + validoxylamine B (39318-73-5,81691-72-7,81739-22-2) + validamycin A (37248-47-8)

Guidance literature:

With Streptomyces hygroscopicus var. limoneus; In water; at 28 ℃; for 168h; Further byproducts.;

DOI:10.1021/ja003643n

Reference yield:

D-Glucose (2280-44-6) → validamine (32780-32-8) + valienamine (38231-86-6) + validamycin A (37248-47-8) + validamycin B

Guidance literature:

With Streptomyces hygroscopicus var. limoneus; In water; at 28 ℃; for 168h; Further byproducts.;

DOI:10.1021/ja003643n

Reference yield:

7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A (86733-63-3) → validamycin A (37248-47-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 6h;

upstream raw materials:

7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A

validamycin A undeca-O-acetate

validamycin A undecabenzyl ether

D-Glucose

Downstream raw materials:

1L-(1,2,4/3)-1-Methyl-2,3,4-cyclohexantriol

5a-carba-1,5-anhydro-L-iditol

N-(tert-butyloxycarbonyl)-valienamide

(+)-validoxylamine A

Refernces

• 1、 Dong,Mahmud,Tornus,Lee,Floss. "Biosynthesis of the validamycins: Identification of intermediates in the biosynthesis of validamycin A by Streptomyces hygroscopicus var. limoneus". . p. 2733 - 2742. Retrieved 2007/10/03.
• 2、 Ogawa, Seiichiro,Nose, Taisuke,Ogawa, Takao,Toyokuni, Tatsushi,Iwasawa, Yoshikazu,Suami, Tetsuo. "Synthetic Studies on Antibiotic Validamycins. Part 11. Synthesis of Validamycin A". . p. 2369 - 2374. Retrieved 2007/10/02.