20208-73-5

Usage

Uses

Used in Diagnostics:
N-(1-oxobutyl)glycine is used as a diagnostic marker for inborn errors of metabolism (IEM). Its presence in biological samples can help identify and monitor various metabolic disorders.
Used in Pharmaceutical Industry:
N-(1-oxobutyl)glycine is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs targeting specific metabolic pathways.
Used in Research:
N-(1-oxobutyl)glycine is used as a research tool to study the role of acylglycines in cellular metabolism and their potential implications in disease processes. This can lead to a better understanding of metabolic disorders and the development of targeted therapies.

InChI:InChI=1/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)

Upstream product

• 106-31-0 butanoic acid anhydride 
• 56-40-6 glycine 
• 107-92-6 butyric acid 
• 90205-46-2 ethyl 2-butyramidoacetate 
• 141-75-3 butyryl chloride 

Downstream Products

• 1527499-46-2 1-butyryl-3-(1-hydroxy-3-(4-(methylthio)phenyl)propylidene)pyrrolidine-2,4-dione 
• 1626437-83-9 N-(3-(1-butyryl-2,4-dioxopyrrolidin-3-ylidene)-3-hydroxypropyl)-4-methylbenzenesulfonamide 
• 1443676-88-7 (Z)-5-(4-hydroxybenzylidene)-3-methyl-2-propyl-3,5-dihydro-4H-imidazol-4-one 

Relevant academic research and scientific papers

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

A Convenient Protocol for the Synthesis of Fatty Acid Amides

Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.

A detailed study of antibacterial 3-acyltetramic acids and 3-acylpiperidine-2,4-diones

Inspired by the core fragment of antibacterial natural products such as streptolydigin, 3-acyltetramic acids and 3-acylpiperidine-2,4-diones have been synthesised from the core heterocycle by direct acylation with the substituted carboxylic acids using a strategy which permits ready access to a structurally diverse compound library. The antibacterial activity of these systems has been established against a panel of Gram-positive and Gram-negative bacteria, with activity mostly against the former, which in some cases is very potent. Data consistent with modes of action against undecaprenylpyrophosphate synthase (UPPS) and/or RNA polymerase (RNAP) for a small subset of the library has been obtained. The most active compounds have been shown to exhibit binding at known binding sites of streptolydigin and myxopyronin at UPPS and RNAP. These systems offer potential for their antibacterial activity, and further demonstrate the use of natural products as biologically validated starting points for drug discovery.

Agonists for Antimicrobial Peptide Systems

Short chain fatty acids (SCFAs) and glycerol esters of SCFAs not previously used for that purpose are provided for use as a medicament for treating, preventing or counteracting microbial infections in animals, including humans, by stimulating the innate antimicrobial peptide defense system. Preferred compounds include phenyl substituted short chain fatty acids (SCFAs) derivatives and. Also provided are methods and compositions for treating, preventing or counteracting microbial infections, including bacterial, viral, fungal, and parasitic infections, by administration of medicaments comprising a secretagogue-effective amount of the compounds of the invention.

Evidence for substrate preorganization in the peptidylglycine α-amidating monooxygenase reaction describing the contribution of ground state structure to hydrogen tunneling

Peptidylglycine α-amidating monooxygenase (PAM) is a bifunctional enzyme which catalyzes the post-translational modification of inactive C-terminal glycine-extended peptide precursors to the corresponding bioactive α-amidated peptide hormone. This conversion involves two sequential reactions both of which are catalyzed by the separate catalytic domains of PAM. The first step, the copper-, ascorbate-, and O2-dependent stereospecific hydroxylation at the α-carbon of the C-terminal glycine, is catalyzed by peptidylglycine α-hydroxylating monooxygenase (PHM). The second step, the zinc-dependent dealkylation of the carbinolamide intermediate, is catalyzed by peptidylglycine amidoglycolate lyase. Quantum mechanical tunneling dominates PHM-dependent Cα-H bond activation. This study probes the substrate structure dependence of this chemistry using a set of N-acylglycine substrates of varying hydrophobicity. Primary deuterium kinetic isotope effects (KIEs), molecular mechanical docking, alchemical free energy perturbation, and equilibrium molecular dynamics were used to study the role played by ground-state substrate structure on PHM catalysis. Our data show that all N-acylglycines bind sequentially to PHM in an equilibrium-ordered fashion. The primary deuterium KIE displays a linear decrease with respect to acyl chain length for straight-chain N-acylglycine substrates. Docking orientation of these substrates displayed increased dissociation energy proportional to hydrophobic pocket interaction. The decrease in KIE with hydrophobicity was attributed to a preorganization event which decreased reorganization energy by decreasing the conformational sampling associated with ground state substrate binding. This is the first example of preorganization in the family of noncoupled copper monooxygenases.

Solid phase synthesis of acylglycine human metabolites

Acylglycines represents a large and important class of human metabolites. They are often used in medicine to identify fatty acid oxidation disorders. A highly efficient solid phase synthesis approach to obtain these clinically important compounds is devel

Compounds that stimulate glucose utilization and methods of use

The invention provides novel compounds of the Formula (I) that stimulate rates of glucose oxidation in myocardial cells. The invention also relates to pharmaceutical compositions comprising compounds capable of stimulation of glucose oxidation, methods for increasing glucose oxidation rates in myocardial cells, and methods of treatment of myocardial ischemia wherein W is C1-C6 alkyl, halogen, or argyl; Cyc is C3 or C4 cycloalkyl; p is 0-3 for Cyc being C4 cycloalkyl and p=0-2 for Cyc being C3 cycloalkyl; Y is O, S, or NR, where R═H, alkyl or aryl; X is O, S, NR, or CR3R4; Z is H, alkyl, cycloalkyl, aryl or (cyclo)alkylcarbonyl; R1 is H, alkyl, aryl or O; R2 is H, alkyl or aryl; R3 and R4 are, independently, H, alkyl or aryl; and n is an integer from 1 to 10; or a pharmaceutically acceptable salt, ester or prodrug thereof.

Antipsychotic drug

The present invention provides an antipsychotic drug containing essentially an N-acyl amino acid derivative represented by the following general formula:RCO-Awherein R indicates an alkyl or alkenyl having 1-25 carbon atoms, and A is an amino acid residue. The compound is similar to natural products and has little side effect by acting directly to brain cells after passing through easily the blood brain barrier.

N-Acylglycines: Gas chromatographic mass spectrometric identification and determination in urine by selected ion monitoring

Eleven biologically interesting N-acylglycines have been synthesized and the gas chromatographic and mass spectrometric properties of their trimethylsilyl derivatives studied. A sharp and reproducible gas chromatographic peak could be obtained for each n-acylglycine as the N,O-bis(trimethylsilyl)-N-acylglycine. By the use of these derivatives a sensitive and specific selected ion monitoring method for the determination of N-acylglycines in human urine has been developed.