310404-45-6

Basic information

• Product Name: Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)-
• Synonyms: Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)-;3-dioxo-2H-isoindol-2-yl)oxy]-4-Methyl-;(R)-2-(1,3-Dioxoisoindolin-2-yloxy)-4-methylpentanoic acid
• CAS NO: 310404-45-6
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.27
• Product Categories: API intermediates
• Mol File: 310404-45-6.mol

Chemical Properties

• Boiling Point: 445.01°C at 760 mmHg
• Flash Point: 222.935°C
• Appearance: /
• Density: 1.355g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)-(310404-45-6)
• EPA Substance Registry System: Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)-(310404-45-6)

Safety Data

• Hazardous Substances Data: 310404-45-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)is used as a key intermediate in the synthesis of pharmaceutical compounds for its unique structural features and chiral properties. Its ability to participate in specific chemical reactions and form stable complexes with biological targets makes it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)is utilized as a building block for the creation of novel agrochemicals with targeted pest control properties. Its complex structure allows for the design of molecules with specific modes of action, potentially leading to more effective and environmentally friendly pest management solutions.
Used in Chiral Synthesis:
Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)is employed as a chiral synthon in asymmetric synthesis, providing a convenient and enantioselective approach to access a variety of biologically active compounds. Its unique stereochemistry and functional groups enable the development of enantiomerically pure molecules with potential applications in various fields, including medicine, fragrances, and flavorings.
Used in Research and Development:
Pentanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-4-methyl-,(2R)serves as a valuable research tool in the study of stereochemistry, organic synthesis, and molecular recognition. Its unique structure and properties allow scientists to explore new reaction pathways, develop innovative synthetic methods, and gain insights into the behavior of chiral molecules in biological systems.

InChI:InChI=1/C14H15NO5/c1-8(2)7-11(14(18)19)20-15-12(16)9-5-3-4-6-10(9)13(15)17/h3-6,8,11H,7H2,1-2H3,(H,18,19)/t11-/m1/s1

Upstream product

• 61-90-5 L-leucine 
• 37755-48-9 benzyl (2S)-2-hydroxy-4-methylpentanoate 
• 3069-51-0 L-α-Acetoxyisocapronsaeure-tert-butylester 
• 3069-52-1 (2S)-2-hydroxy-4-methylpentanoic acid 1,1-dimethylethyl ester 
• 3069-50-9 O-acetyl-L-α-hydroxyisocapric acid 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 380886-35-1 D-tert-butyl 2-phthalimid-N-oxy-4-methylpentanoate 
• 310404-40-1 benzyl (R)-4-methyl-2-phthalimidooxypentanoate 

Downstream Products

• 627079-37-2 (S)-2-[(R)-2-((R)-2-Benzyloxycarbonylamino-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester 
• 627079-36-1 (S)-2-[(R)-2-((S)-2-Benzyloxycarbonylamino-propionylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester 
• 627079-35-0 (S)-2-[(R)-2-(2-Benzyloxycarbonylamino-acetylaminooxy)-4-methyl-pentanoylaminooxy]-3-phenyl-propionic acid tert-butyl ester 
• 500800-65-7 (S)-2-((R)-2-Aminooxy-4-methyl-pentanoylaminooxy)-3-phenyl-propionic acid tert-butyl ester 
• 380886-45-3 D-p-chlorophenyl 2-phthalimidoxy-4-methylpentanoamide 

Relevant articles and documents

Disulfide bond creates a small connecting loop in aminoxy peptide backbone

Disulfide-bond formation between the side chains of cysteine-cysteine pairs is often critical to the folding behavior, stability, and functionality of proteins. In this paper, we report that sulfur atoms can be introduced into the amide groups of aminoxy peptides to form a novel type of disulfide bridge, which creates a connecting loop in the peptide backbone.

AMINOXY ACID-BASED ANTI-CANCER STEM CELL COMPOUNDS AND METHODS THEREOF

Provided are synthetic small molecules and their use as drug, in particular in the treatment of cancer. Also provided is a method of inhibiting cancer stem cells. Also provided is a method for treatment of cancers and other diseases by affecting mitochondrial functions. Also provided is a method of making and using of the compounds.

α-Aminoxy Oligopeptides: Synthesis, Secondary Structure, and Cytotoxicity of a New Class of Anticancer Foldamers

α-Aminoxy peptides are peptidomimetic foldamers with high proteolytic and conformational stability. To gain an improved synthetic access to α-aminoxy oligopeptides we used a straightforward combination of solution- and solid-phase-supported methods and obtained oligomers that showed a remarkable anticancer activity against a panel of cancer cell lines. We solved the first X-ray crystal structure of an α-aminoxy peptide with multiple turns around the helical axis. The crystal structure revealed a right-handed 28-helical conformation with precisely two residues per turn and a helical pitch of 5.8 ?. By 2D ROESY experiments, molecular dynamics simulations, and CD spectroscopy we were able to identify the 28-helix as the predominant conformation in organic solvents. In aqueous solution, the α-aminoxy peptides exist in the 28-helical conformation at acidic pH, but exhibit remarkable changes in the secondary structure with increasing pH. The most cytotoxic α-aminoxy peptides have an increased propensity to take up a 28-helical conformation in the presence of a model membrane. This indicates a correlation between the 28-helical conformation and the membranolytic activity observed in mode of action studies, thereby providing novel insights in the folding properties and the biological activity of α-aminoxy peptides.

Chiral α-aminoxy acid/achiral cyclopropane α-aminoxy acid unit as a building block for constructing the α N-O helix

(Figure Presented) The monomer 1 derived from achiral 1-(aminoxy) cyclopropanecarboxylic acid (OAcc) and oligopeptides 2-9 consisting of a chiral α-aminoxy acid and an achiral α-aminoxy acid such as OAcc were synthesized and their structures characterized. The eight-membered-ring intramolecular hydrogen bond, namely the α N-O turn, was formed between adjacent residues independent of their chirality. However, the helix formation was sequence-dependent. Dipeptide 2 bearing chiral α-aminoxy acid (d-OAA) at the N-terminus and achiral OAcc at the C-terminus preferentially adopted a right-handed 1.88 helical structure, but dipeptide 3 (OAcc-d-OAA) did not. Theoretical calculation results, in good agreement with experimental ones, revealed that the biased handedness of α N-O turn found in OAcc residue depends on its preceding chiral residue. It was then found that the helical conformation was destroyed in the case of oligopeptides 6 and 7 [OAA-(OAcc) n, n = 2, 3]. The crystal structure of tripeptide 8 ( iPrCO-d-OVal-OAcc-d-OVal-NHiBu) further disclosed the helical structure formed by three consecutive homochiral α N-O turns. This study has uncovered achiral aminoxy acid residues such as the OAcc unit as a useful building block to be incorporated into chiral aminoxy peptides to mimic chiral helix structure.

Synthetic Ion Channels

Provided herein are self-assembling compounds that can form ion channels in lipid bilayers or cell membranes and ion-channel-forming compositions comprising the self-assembling compounds. Also provided are methods of making and using the ion channels formed from a plurality of molecules of the self-assembling compounds. Further, provided are methods of treating or preventing conditions and diseases that are related to the dysfunction of ion channels, including chloride channels.

Synthesis of chiral β3-aminoxy peptides

A series of chiral β3-aminoxy acids or amides with various side chains have been synthesized via two different approaches. One is the Arndt-Eistert homologation approach, using chiral α-aminoxy acids as starting materials. The other approach, utilizing the enantioselective reduction of β-keto esters catalyzed by baker's yeast or chiral Ru(II) complexes, produces chiral β3-aminoxy acids with nonproteinaceous side chains. The oligomers of β3-aminoxy acids can be readily prepared using EDCI/HOAt as the coupling reagent.

A Reverse Turn Structure Induced by a D,L-α-Aminoxy Acid Dimer

Our previous work revealed that two adjacent D-α-aminoxy acids could form two homochiral N-O turns, with the backbone folding into an extended helical structure (1.88-helix). Here, we report the conformational studies of linear peptides 3-6, wh

Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids

Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral α-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.