D-ALPHA-HYDROXYISOVALERIC ACID

Name: D-ALPHA-HYDROXYISOVALERIC ACID
SKU: ACM17407566
Rating: 5 (1 reviews)

CAS

17407-56-6

Catalog Number

ACM17407566

Category

Main Products

Molecular Weight

118.13

Molecular Formula

C5H10O3

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Specification

Synonyms

D-alpha-Hydroxyisovaleric acid

Appearance

White to Off White powder

Stereocomplexation of PLA-Substituted Oligomers Such as Oligo(α-Hydroxyisovaleric Acid)

Andersson, Sofia Regnell, et al. Polymer, 2013, 54(16), 4105-4111.

Researchers synthesized two oligomeric enantiomers from both α-hydroxyisovaleric acid and lactic acid and then created two part blends from all possible oligomer pairings. The PLA-like oligomer known as oligo(a-hydroxyisovaleric acid) was found to undergo stereocomplexation between its two enantiomers. Separate oligomers exhibited different crystal structures than the enantiomeric blend which demonstrates stereocomplexation.
Preparation of oligomers
· Oligo(L-lactic acid) (L-OLA), oligo(D-lactic acid) (D-OLA), oligo(L-α-hydroxyisovaleric acid) (L-OHVA), and oligo(D-α-hydroxyisovaleric acid) (D-OHVA) were synthesized via the polycondensation of about 4 g of monomer in bulk, employing 1.5 mol% of p-toluenesulfonic acid as a catalyst.
· For the oligo(hydroxyisovaleric acid)s, L-α-hydroxyisovaleric acid and D-α-hydroxyisovaleric acid were used as the monomers. During the initial reaction, which lasted 6 hours at 180°C under nitrogen flow and atmospheric pressure, methanol, water, and/or hydrochloric acid were eliminated. In the subsequent phase, the pressure was lowered to 30 Pa over 1.5 hours, continuing the reaction for an additional 28 hours to achieve the polymerization of oligo(hydroxyisovaleric acid)s. The resulting oligomers were purified by precipitation using chloroform and a methanol-water mixture (10:1 volume%).

D-α-Hydroxyisovaleric Acid Used in the Production of Valinomycin Through the Biosynthetic Pathway

Jaitzig, Jennifer, et al. ACS synthetic biology, 2014, 3(7), 432-438.

Valinomycin represents a cyclic oligomeric peptide (COD) which exhibits multiple biological activities and Streptomyces strains produce it. The dodecapeptide displays 3-fold rotational symmetry and consists of D-α-hydroxyisovaleric acid-D-valine-L-lactic acid-L-valine monomers with alternating amide and ester bonds. Scientists previously discovered the gene cluster responsible for valinomycin biosynthesis and developed a corresponding biosynthetic model.
Early feeding experiments with Streptomyces valinomycin producer strains showed that L-Val serves as a precursor for both the L- and D-forms of valine in valinomycin. However, these studies did not clearly identify the direct precursors for the two hydroxy acid components of valinomycin, namely D-α-hydroxyisovaleric acid (D-Hiv) and L-lactate (L-Lac). Additionally, comparing the binding pocket residues of the respective A domains did not yield accurate predictions of substrate binding specificities. The proposed biosynthesis of the α-hydroxy acids from α-amino acids occurs through deamination to form the corresponding keto acids, followed by reduction.

What is the molecular formula of D-alpha-hydroxyisovaleric acid?

The molecular formula of D-alpha-hydroxyisovaleric acid is C5H10O3.

What are the synonyms of D-alpha-hydroxyisovaleric acid?

The synonyms of D-alpha-hydroxyisovaleric acid are 17407-56-6, (R)-2-hydroxy-3-methylbutanoic acid, (2R)-2-hydroxy-3-methylbutanoic acid, and (R)-2-hydroxy-3-methylbutyric acid.

What is the molecular weight of D-alpha-hydroxyisovaleric acid?

The molecular weight of D-alpha-hydroxyisovaleric acid is 118.13 g/mol.

What is the IUPAC name of D-alpha-hydroxyisovaleric acid?

The IUPAC name of D-alpha-hydroxyisovaleric acid is (2R)-2-hydroxy-3-methylbutanoic acid.

What is the InChI of D-alpha-hydroxyisovaleric acid?

The InChI of D-alpha-hydroxyisovaleric acid is InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m1/s1.

How many hydrogen bond donor counts does D-alpha-hydroxyisovaleric acid have?

D-alpha-hydroxyisovaleric acid has 2 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does D-alpha-hydroxyisovaleric acid have?

D-alpha-hydroxyisovaleric acid has 3 hydrogen bond acceptor counts.

What is the XLogP3-AA value of D-alpha-hydroxyisovaleric acid?

The XLogP3-AA value of D-alpha-hydroxyisovaleric acid is 0.5.