38665-10-0

Basic information

• Product Name: Validoxylamine A
• Synonyms: 1,5,6-Trideoxy-5-hydroxymethyl-1-[[(1S)-4β,5α,6β-trihydroxy-3-hydroxymethyl-2-cyclohexen-1β-yl]amino]-D-chiro-inositol
• CAS NO: 38665-10-0
• Molecular Formula: C₁₄H₂₅NO₈
• Molecular Weight: 335.35
• Mol File: 38665-10-0.mol

Chemical Properties

• Boiling Point: 602.6°C at 760 mmHg
• Flash Point: 222.6°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 4.92E-17mmHg at 25°C
• Refractive Index: 1.675
• CAS DataBase Reference: Validoxylamine A(CAS DataBase Reference)
• NIST Chemistry Reference: Validoxylamine A(38665-10-0)
• EPA Substance Registry System: Validoxylamine A(38665-10-0)

Safety Data

• Hazardous Substances Data: 38665-10-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Validoxylamine A is used as a fungicide for controlling various fungal diseases in crops. Its application helps protect plants from harmful fungi, thereby ensuring a healthy growth and increased yield.
Used in Pharmaceutical Industry:
Validoxylamine A is used as a potential antibiotic agent for treating bacterial infections. Its effectiveness against certain bacteria makes it a valuable compound in the development of new antibiotics, especially in the face of increasing antibiotic resistance.
Used in Research and Development:
Validoxylamine A is also utilized in research and development for its potential applications in both agriculture and medicine. Scientists are exploring its properties and interactions with other compounds to enhance its effectiveness and develop new formulations for various uses.

InChI:InChI=1/C14H25NO8/c16-3-5-1-7(11(20)13(22)9(5)18)15-8-2-6(4-17)10(19)14(23)12(8)21/h1,6-23H,2-4H2

Upstream product

• 117295-72-4 2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidene-6-p-toluenesulphenylvalidoxylamine A 
• 37248-47-8 validamycin A 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 117295-71-3 (1S,2R,5R,7R,8S,10S)-8,9-dibenzyloxy-11-<(1S)-(1,4,6/5)-4,5,6-tribenzyloxy-3-benzyloxymethylcyclohex-2enyl>-5-phenyl-4,6-dioxa-11-azatricyclo<8.1.0.0.^2,7>undecane 
• 117320-21-5 2,3,4',5',6',7'-hexa-O-benzyl-4,5-O-benzyllidenevalidoxylamine B 
• 114779-35-0 (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane 
• 114779-35-0 (1aR,2S,3S,3aR,5R,7aS,7bR)-2,3-Bis-benzyloxy-5-phenyl-hexahydro-1,4,6-trioxa-cyclopropa[a]naphthalene 
• 79527-24-5 Validoxamine A Octaacetate 
• 81692-23-1 N-<(1SR)-(1,4,6/5)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1RS)-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexylamine nonaacetate 
• 81692-23-1 N-<(1SR)-(1,4,6/5)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexylamine nonaacetate 
• 79527-23-4 Acetic acid (1R,2S,5S,6R)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester 
• 79527-23-4 Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-cyclohex-3-enyl ester 
• 70878-41-0 DL-1,2,3-tri-O-acetyl-(1,3/2,4,6)-6-acetoxymethyl-4-bromo-1,2,3-cyclohexanetriol 
• 79527-13-2 DL-(1,3/2,4,6)-4-bromo-6-hydroxymethyl-1,2,3-cyclohexanetriol 

Downstream Products

• 68108-50-9 (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane 
• 124330-59-2 (4R,5R)-2,4-diacetoxy-5-acetoxymethylcyclohex-2-en-1-one 
• 74645-52-6 (1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol 
• 79527-24-5 validoxylamine A octa-O-acetate 
• 639852-30-5 (2R,3S,4R,5R)-2,3,4-tris(trimethylsilyloxy)-5-[(trimethylsilyloxy)methyl]cyclohexanone 
• 37248-47-8 validamycin A 
• 1039021-94-7 4''-epi-validamycin A 
• 102069-51-2 C₂₁H₂₉NO₈ 
• 114779-32-7 1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene 
• 139499-19-7 2,3,4,7-tetra-O-benzylvalidamine 
• 124330-57-0 (2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexanone 
• 110391-10-1 (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one 
• 137063-37-7 ((1R,2R,3S,4S,5S)-2,3,4-tris(benzyloxy)-5-(((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)amino)cyclohexyl)methanol 
• 86756-42-5 (4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenyl-N-((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)hexahydro-4H-benzo[d][1,3]dioxin-6-amine 

Relevant articles and documents

Molecular basis for trehalase inhibition revealed by the structure of trehalase in complex with potent inhibitors

Strong inhibitions: The inhibition of trehalases, enzymes which hydrolyze the disaccharide trehalose, is a target for novel antibiotic insecticides. The structures (see picture; C black, N blue, O red, S yellow) of a trehalase in complex with validoxylami

Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis

Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7′-phosphate with net retention of the 'anomeric configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7′-phosphate to validoxylamine A.

Synthesis of [7-3H]valienamine, [7-3H]valienone, [7-3H]valiolamine and [7-3H]valiolone from validamycin A

To investigate the biosynthetic pathway to the cyclitol moieties of acarbose and validamycin A, [7-3H]valienamine, [7-3H]valienone, [7-3H]valiolamine and [7-3H]valiolone were synthesized as plausible precursors. Valienamine together with validamine was isolated from the degradation of validamycin A by Flavobacterium saccharophilum and served as starting material for the synthesis. Validamine was removed partially at the stage of tritylation and completely after the oxidation of the primary hydroxy group at C-7 to the aldehyde. The resulting valienamine aldehyde was reduced with tritiated sodium borohydride to produce [7-3H]valienamine. The latter was converted to [7-3H]valiolamine by a synthetic route described in the literature. The 3H-labeled amines were oxidized to [7-3H]valienone and [7-3H]valiolone, respectively, using 3,5-di-tert-butyl-1,2-bezoquinone (DBQ) followed by hydrolysis with oxalic acid.

Synthetic studies on antibiotic validamycins. Part 13. Total synthesis of (+)-validamycins A and E, and related compounds

(+)-Validoxylamine A (1) has been completely synthesized by deoxygenation of the validoxylamine B derivative (6) through formation of the aziridine, nucleophilic displacement with toluenethiol, reduction with Raney nickel, and deprotection. The validoxylamine A derivative (10) obtained was convertible, by glycosylation followed by deprotection, into validamycins A (2), E (3), and their analogues, which constitutes a total synthesis thereof.

Total Synthesis of (+)-Validoxylamine A

(+)-Validoxylamine A was synthesized by selective deoxygenation of (+)-validoxylamine B derivative, which was obtained by the coupling of the partially protected (+)-valienamine and (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo8.

Synthetic Studies on the Validamycines. 10. Total Synthesis of DL-Validoxylamines A and B.

The first synthesis of racemic validoxylamine A (3) and B (4), constituents of antibiotic validamycins, is described.For construction of these types of pseudodisaccharides containing an imino linkage, a coupling reaction of the protected anhydro derivative of DL-pentahydroxy(hydroxymethyl)cyclohexane (5) with the DL-trihydroxy(hydroxymethyl)cyclohexylamine or -cyclohexenylamine (6 or 7) was untertaken.All possible diastereoisomers (four pairs of enantiomeres) formed by the reaction of 5 with 6, employed for synthesis of 4, could be separated by chromatography on silica gel, and the relative configuration in two of the enantiomeric pairs, deduced on the basis of 1H-NMR spectroscopy, were confirmed by identification of one pair with an authentic chiral sample 4.On the other hand, the intermediate enantiomeric pair 13a obtained by a coupling of the appropriate epoxide 5 and amine 7 underwent mainly dehydration with sulfuryl chloride in pyridine to give the pair of enantiomers 19a, one of which was the protected derivative of 3.In contrast, the diastereomeric pair of enantiomers 13b yielded selectively the chloride 18b, which was then transformed into the enantiomeric pair 21b by dehydrochlorination followed by deprotection.

SYNTHESIS OF DL-VALIDOXYLAMINE A

The first total synthesis of DL-validoxylamine A, one of the components of the antibiotic validamycin complex, is described.

SYNTHESIS OF SOME RACEMIC ISOMERS OF VALIDOXYLAMINE A

Two racemic isomers of validoxylamine A were synthesized by the condensation reaction of the blocked DL-validamine and the allyl bromide, the precursor of the unsaturated branched-chain cyclitol moiety.