2280-42-4

Basic information

• Product Name: dl-3-hydroxynorvaline
• Synonyms: α-amino-β-hydroxyvaleric acid;α-Amino-β-hydroxyvaleric acid, 2-Amino-3-hydroxypentanoic acid, 3-Hydroxy-2-aminopentanoic acid, DL-β-Hydroxynorvaline;2-amino-3-hydroxy-valeric acid;2-azanyl-3-hydroxy-pentanoic acid;3-Hydroxy-DL-norvaline;beta-Hydroxynorvaline;DL-2-Amino-3-hydroxyvaleric acid
• CAS NO: 2280-42-4
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.15
• Mol File: 2280-42-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 231.2℃
• Boiling Point: 328.4°Cat760mmHg
• Flash Point: 152.4°C
• Appearance: /
• Density: 1.237g/cm³
• Storage Temp.: −20°C
• PKA: 2.39±0.24(Predicted)
• BRN: 1722350
• CAS DataBase Reference: dl-3-hydroxynorvaline(CAS DataBase Reference)
• NIST Chemistry Reference: dl-3-hydroxynorvaline(2280-42-4)
• EPA Substance Registry System: dl-3-hydroxynorvaline(2280-42-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2280-42-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A non-proteinogenic amino-acid derivative that is norvaline (2-aminopentanoic acid) in which a hydrogen at position 3 is replaced by a hydroxy group.

Biochem/physiol Actions

3-Hydroxynorvaline (HNV) is a microbial, α amino acid threonine analogue which has antiviral activity (herpes virus) and is toxic to mammalian cells (embryotoxic and teratogenic) presumably via incorporation into proteins. 3-Hydroxynorvaline may be used as an unnatural amino acid to study the fidelity of protein translation at the level of acyl-tRNA editing. 3-Hydroxynorvaline may also be used to study enzymes and molecules involved in threonine metabolism.

Upstream product

• 123-38-6 propionaldehyde 
• 32817-15-5 copper(II) glycinate 
• 116637-05-9 acetylamino-malonic acid monomethyl ester 
• 2983-07-5 Ethyl-(1,2-diacetoxy-butyl)-ether 
• 151-50-8 potassium cyanide 
• 854657-46-8 2-bromo-3-methoxy-valeric acid 
• 1439368-22-5 ethyl 2-(tert-butoxycarbonylamino)-3-oxo-pentanoate 
• 13991-37-2 trans-2-pentenoic acid 

Downstream Products

• 62772-39-8 (+/-)-erythro-2-amino-3-hydroxy-valeric acid ethyl ester 
• 2076-43-9 (+/-)-erythro-β-hydroxynorvaline 
• 2076-43-9 (+/-)-threo-β-hydroxynorvaline 
• 99092-43-0 2-Benzyloxycarbonylamino-3-hydroxy-pentanoic acid 
• 760-78-1 2-aminopentanoic acid 

Relevant articles and documents

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Modular solid-phase synthesis of teroxazoles as a class of α-helix mimetics

α-Helices are ubiquitous structural elements of proteins and are important in molecular recognition. Small molecules mimicking α-helices have proven to be valuable biophysical probes or modulators of protein-protein interactions. Here, we present modeling studies and the modular solid-phase synthesis of teroxazole derivatives as a new class of α-helix mimetics. The synthesis is compatible with a variety of functional groups and should thus be generally applicable for generating diversely substituted oligo-oxazole scaffolds. The teroxazole scaffold is predicted to be polar and to project peptidomimetic side chains at positions i, i+3, and i+6 of an α-helix, which complements projection patterns of existing helix mimetics. The scaffold retains sufficient conformational flexibility to conform to induced-fit models of protein-protein interaction inhibition. Copyright

Synthesis of aliphatic 2-amino-3-hydroxy acids and separation of their diastereoisomers with the aid of copper chelates.

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