26911-39-7

Basic information

• Product Name: 5-hydroxy-4-oxo-L-norvaline
• Synonyms: Ri-331;Antibiotic ri-331;5-Hydroxy-4-oxo-L-norvaline;L-Norvaline, 5-hydroxy-4-oxo-;delta-Hydroxy-gamma-oxo-L-norvaline;Levulinic acid, 2-amino-5-hydroxy-, L- (8ci)
• CAS NO: 26911-39-7
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.1293
• Mol File: 26911-39-7.mol

Chemical Properties

• Boiling Point: 363.8°C at 760 mmHg
• Flash Point: 173.8°C
• Density: 1.409g/cm³
• Vapor Pressure: 9.14E-07mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 5-hydroxy-4-oxo-L-norvaline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-4-oxo-L-norvaline(26911-39-7)
• EPA Substance Registry System: 5-hydroxy-4-oxo-L-norvaline(26911-39-7)

Safety Data

• Hazardous Substances Data: 26911-39-7(Hazardous Substances Data)

Upstream product

• 152685-29-5 4-<3-(formyloxy)-2-oxopropyl>-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one 
• 146197-81-1 (S)-2,2-Bis(trifluormethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-on 
• 142683-60-1 tert-butyl (S)-2-benzyloxycarbonylamino-5-tert-butyldimethylsiloxy-4-oxopentanoate 
• 142683-59-8 tert-butyl (2S,4S)-2-benzyloxycarbonylamino-5-tert-butyldimethylsiloxy-4-hydroxypentanoate 
• 142683-56-5 tert-butyl (S)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentenoate 
• 142683-61-2 tert-butyl (S)-2-benzyloxycarbonylamino-5-hydroxy-4-oxopentanoate 
• 142683-57-6 tert-butyl (S)-2-benzyloxycarbonylamino-4,5-dihydroxy-2-pentenoate 
• 157695-66-4 (S)-2-Benzyloxycarbonylamino-5-hydroxy-4-oxo-pentanoic acid 
• 142683-58-7 tert-butyl (S,Z)-2-benzyloxycarbonylamino-5-tert-butyldimethylsiloxy-4-hydroxy-2-pentenoate 
• 98432-06-5 L-N-Acetyl-δ-hydroxy-γ-oxonorvalin 

Downstream Products

• 7599-99-7 3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one 
• 56-84-8 L-Aspartic acid 

Relevant articles and documents

Antifungal dipeptides incorporating an inhibitor of homoserine dehydrogenase

The antifungal activity of 5-hydroxy-4-oxo-l-norvaline (HONV), exhibited under conditions mimicking human serum, may be improved upon incorporation of this amino acid into a dipeptide structure. Several HONV-containing dipeptides inhibited growth of human pathogenic yeasts of the Candida genus in the RPMI-1640 medium, with minimal inhibitory concentration values in the 32 to 64?μg?mL?1 range. This activity was not affected by multidrug resistance that is caused by overexpression of genes encoding drug efflux proteins. The mechanism of antifungal action of HONV dipeptides involved uptake by the oligopeptide transport system, subsequent intracellular cleavage by cytosolic peptidases, and inhibition of homoserine dehydrogenase by the released HONV. The relative transport rates determined the anticandidal activity of HONV dipeptides.

Synthesis of γ-oxo α-amino acids from L-aspartic acid

The synthesis of different γ-oxo α-amino acids from hexafluoroacetone protected L-aspartic acid chloride 1 via Stille cross coupling reaction is described. Stille reaction of 1 with vinyltributyltin followed by Lewis acid catalyzed intramolecular Michael addition provides access to 4-substituted pipecolic acid derivatives. An efficient synthesis of 5-hydroxy-4-oxo-L-norvaline 7 and a new approach to the 4-oxo-L-ornithine skeleton starting from 1 have been elaborated.

An efficient synthesis of 5-hydroxy-4-oxo-L-norvaline from L-aspartic acid

A synthesis of the antibiotic (-)-HON (5-hydroxy-4-oxo-L-norvaline, RI-331) from L-aspartic acid using hexafluoroacetone as protecting reagent is described.

Stereoselective syntheses of the antibiotics (+)-negamycin and (-)-HON (RI-331)

The stereoselective syntheses of the antibiotics (-)-HON (5-hydroxy-4-oxo-L-norvaline, RI-331) and (+)-negamycin starting from (S)-4-[(Z)-2-(benzyloxycarbonylamino)-2-(tert-butoxycarbonyl)vinyl]-2, 2-dimethyl-1,3-dioxolane and (R)-3-benzyloxycarbonyl-5-[(Z)-2-(tert-butoxycarbonylamino)-2-(methoxy carbonyl) vinyl]-2,2-dimethyl-1,3-oxazolidine, respectively, are described.