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Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-Hydroxyvaleric acid is used as an active pharmaceutical ingredient for the development of various medications due to its unique chemical structure and properties.
Used in Agricultural Chemical Industry:
(2R)-2-Hydroxyvaleric acid is used as a key component in the formulation of agricultural chemicals, contributing to their effectiveness in crop protection and enhancement.
Used as a Flavoring Agent:
(2R)-2-Hydroxyvaleric acid is used as a flavoring agent in the food and beverage industry, providing a distinct taste and aroma to various products.
Used in Synthesis of Organic Compounds:
(2R)-2-Hydroxyvaleric acid is used as a building block in the synthesis of a wide range of organic compounds, including specialty chemicals and intermediates.
Used in Production of Biopolymers:
(2R)-2-Hydroxyvaleric acid has potential applications in the production of biopolymers, which are environmentally friendly alternatives to traditional plastics.
Used as a Chiral Building Block:
(2R)-2-Hydroxyvaleric acid is used as a chiral building block for the synthesis of various compounds, particularly in the pharmaceutical and chemical industries, where enantioselectivity is crucial for the desired biological activity.

Upstream product

• 2013-12-9 D-norvaline 
• 10021-63-3 (R)-(+)-2-hydroxypentanenitrile 
• 89426-81-3 (1S,2S,6R,7R)-4-(1-Methoxymethoxy-butyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 1821-02-9 2-oxopentanoic acid 
• 617-31-2 2-hydroxyvaleric acid 
• 133964-76-8 (S)-2-Hydroxy-pentanoic acid methylamide 
• 219598-64-8 (2S)-2-(hydroxymethyl)-1-[(2S)-2-hydroxypentanoyl]pyrrolidine 
• 140632-58-2 (R)-(E)-2-hydroxy-3-pentenoic acid 
• 6812-26-6 (R)-(-)-2-hydroxy-3-(E)-pentenenitrile 
• 60-29-7 diethyl ether 
• 207223-21-0 (2S,5S,6R)-2-propyl-2-hydroxy-4,5-dimethyl-6-phenylmorpholin-3-one 
• 207223-39-0 (2S,5S,6R)-4,5-Dimethyl-6-phenyl-2-propyl-morpholin-3-one 
• 207223-31-2 (5S,6R)-4,5-Dimethyl-6-phenyl-2-prop-(Z)-ylidene-morpholin-3-one 
• 267417-23-2 (2S)-1-[(2R)-2-allyl-2-hydroxyacetyl]-2-(hydroxymethyl)pyrrolidine 

Downstream Products

• 1026504-17-5 (R)-2-Oxo-2-(3-phenyl-propyl)-5-propyl-2λ⁵-[1,3,2]dioxaphospholan-4-one 
• 152830-23-4 (2R)-2-(((3-phenylpropyl)hydroxyphosphoryl)oxy)penatnoic acid 
• 152830-15-4 (2R)-2-(((3-phenylpropyl)hydroxyphosphoryl)oxy)pentanoic acid benzyl ester 
• 108340-61-0 (R)-1,2-pentanediol 
• 133420-94-7 [(R)-2-Benzyloxy-pent-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 133420-96-9 2-(Benzyloxy)pentansaeure-ethylester 
• 133420-98-1 (R)-2-benzyloxypentanal 
• 862901-93-7 methyl (R)-2-(4-bromobenzyloxy)pentanoate 

Relevant academic research and scientific papers

Efficient Synthesis of D-Phenylalanine from L-Phenylalanine via a Tri-Enzymatic Cascade Pathway

D-phenylalanine is an important intermediate in food and pharmaceutical industries. Here, to enable efficient D-phenylalanine biosynthesis from L-phenylalanine, a tri-enzymatic cascade was designed and reconstructed in vivo. The activity of Proteus vulgaris meso-diaminopimelate dehydrogenase (PvDAPDH) toward phenyl pyruvic acid was identified as the limiting step. To overcome, the tension in the phenyl pyruvic acid side-chain, PvDAPDH was engineered, generating PvDAPDHW121A/R181S/H227I, whose catalytic activity of 6.86 U mg?1 represented an 85-fold increase over PvDAPDH. Introduction of PvDAPDHW121A/R181S/H227I, P. mirabilis L-amino acid deaminase, and Bacillus megaterium glucose dehydrogenase in E. coli enabled the production of 57.8 g L?1 D-phenylalanine in 30 h, the highest titer to date using 60 g L?1 L-phenylalanine as starting substrate, which meant a 96.3 % conversion rate and >99 % enantioselectivity on a 3-L scale. The proposed tri-enzymatic cascade provides a novel potential bio-based approach for industrial production of D-phenylalanine from cheap amino acids.

Total Synthesis of the Antitumor Depsipeptide FE399 and Its S-Benzyl Derivative: A Macrolactamization Approach

An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.

The substrate spectrum of mandelate racemase: Minimum structural requirements for substrates and substrate model

Mandelate racemase (EC 5.1.2.2) is one of the few biochemically well-characterized racemases. The remarkable stability of this cofactor-independent enzyme and its broad substrate tolerance make it an ideal candidate for the racemization of non-natural α-hydroxycarboxylic acids under physiological reaction conditions to be applied in deracemization protocols in connection with a kinetic resolution step. This review summarizes all aspects of mandelate racemase relevant for the application of this enzyme in preparative-scale biotransformations with special emphasis on its substrate tolerance. Collection and evaluation of substrate structure-activity data led to a set of general guidelines, which were used as basis for the construction of a general substrate model, which allows a quick estimation of the expected activity for a given substrate.

Selective reductions. 59. Effective intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane and intermolecular asymmetric reductions of the corresponding esters with B-chlorodiisopinocampheylborane

A comparison of the stereochemistry of the products obtained from the intramolecular asymmetric reduction of a series of keto acids with (-)-diisopinocampheylborane and intermolecular asymmetric reduction of the corresponding series of keto esters with (-)-B-chlorodiisopinocampheylborane ((-)-DIP-Chloride) has been made. The stereochemistry of the hydroxy acids from the reduction of keto acids is dependent only on the enantiomer of the reagent used. The stereochemistry of the products from the reduction of keto esters is also consistent, except those of aliphatic α-keto esters. α-, β-, and γ-keto acids provide the corresponding hydroxy acids in 77-98% ee, and the α- and γ-keto esters afford the hydroxy esters in 82-≥99% ee. β-Keto esters do not undergo reduction. Although the reduction of δ-keto acids does not proceed under the same reaction conditions, the reduction of δ-keto esters is facile. All of the products from the reduction of γ-keto acids and esters and δ-keto esters were converted to the corresponding lactones. This study revealed that DIP-Chloride is an efficient reagent for the reduction of α-keto esters at low temperatures.

Efficient intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane1

(equation presented) α-, β-, and γ-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The γ-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.

Synthesis and utilisation of chiral 3-hydroxy perhydropyrrolo [2,1-c] [1,4] oxazin-4-one as a novel precursor for the enantioselective synthesis of α-hydroxy carboxylic acids

A novel strategy for the enantioselective synthesis of several α- hydroxy carboxylic acids by the nucleophilic alkylation of chiral 3-hydroxy- (3S, 8aS)-perhydropyrrolo [2,1-C] [1,4] oxazin -4 one is reported.

Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

N-Acylation of prolinol with α-ketoacid chlorides results in concomitant hemiacetalization of the α-keto amide by the prolinol hydroxyl group. (R) or (S) α-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) α-alkyl mandelic acids with good stereoselectivity.

Quantitative transformation of racemic 2-hydroxy acids into (R)-2-hydroxy acids by enantioselective oxidation with glycolate oxidase and subsequent reduction of 2-keto acids with D-lactate dehydrogenase

The enzymatic resolution of chiral 2-hydroxy acids 1 by enantioselective oxidation with molecular oxygen in the presence of glycolate oxidase from spinach (Spinacia oleracea) and subsequent asymmetric reduction of 2-oxo acids 2 with D-lactate dehydrogenase from Lactobacillus leichmannii leads to enantiomerically pure (R)-2-hydroxy acids in up to 89% yield based on the racemate.

Synthesis of optically active α-hydroxy acids by kinetic resolution through lipase-catalyzed enantioselective acetylation

The lipase-catalyzed acetylation of a broad spectrum of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candida antarctica and Burkholderia species, are convenient biocatalysts for the synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to 99%). The absolute configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3. These results establish that (S)-2-hydroxy acids 1 were preferentially acetylated by microbial lipases.