24003-67-6

Usage

Uses

1. Used in Pharmaceutical Industry:
N-(1-oxohexyl)-glycine is used as an acylaminoacid derivative for its antipsychotic properties, offering potential therapeutic benefits in the treatment of psychiatric disorders.
2. Used as a Urinary Biomarker:
N-(1-oxohexyl)-glycine is used as a diagnostic biomarker to indicate deficiencies in medium-chain acyl-CoA dehydrogenase, a crucial enzyme in fatty acid metabolism.
3. Used in Radiation Exposure Detection:
N-(1-oxohexyl)-glycine is used as a biomarker for exposure to gamma radiation, helping in the assessment of radiation exposure levels in individuals.
4. Used in Cancer Research:
Increased levels of N-(1-oxohexyl)-glycine can be observed during cancer, making it a potential biomarker for cancer diagnosis and monitoring.
5. Used in Metabolic Studies:
N-(1-oxohexyl)-glycine is used in research to understand the effects of treatments, such as the PPARα ligand Wy 14643, on metabolic pathways, as its levels can be significantly altered by such treatments.

InChI:InChI=1/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)

Upstream product

• 142-61-0 Hexanoyl chloride 
• 56-40-6 glycine 
• 142-62-1 hexanoic acid 
• 50-00-0 formaldehyd 
• 628-02-4 Caproamide 
• 201230-82-2 carbon monoxide 
• 62005-22-5 ethyl hexanoylglycinate 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 2051-49-2 n-hexanoic anhydride 

Downstream Products

• 31295-09-7 N-hexanoylglycine methyl ester 
• 881-90-3 4-benzylidene-2-methyl-2-oxazolin-5-one 
• 7685-82-7 N-hexanoyl-glycine 4-nitro-phenyl ester 
• 17080-40-9 3-(N-hexanoyl-glycyl)-5,5-dimethyl-2-oxo-thiazolidine-4-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis and binding studies of a 1-alkyl-3,6-diamino-4-quinolone based receptor for N-acylated dipeptides

The synthesis and binding properties of a semirigid host for N-acyldipeptide carboxylic acids is presented. The design is based on the rigidification of a peptide strand, coupled to the use of a substituted quinoline as a hydrogen bond acceptor for the proton of a carboxylic acid.

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.

The relationship between the structure and properties of amino acid surfactants based on glycine and serine

Two series of surfactants based on glycine and serine were synthesized with aproic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid and hexadecanoic acid. All the surfactants were characterized by MS and 1H NMR, the structures of the synthesized surfactants are correct and the signals in MS and 1H NMR can be explained. The reaction conditions, surface properties and foam properties were studied. For the two series of surfactants, critical micelle concentration (CMC) and γ CMC (surface tension at CMC) decrease and surface activity is enhanced as the length of carbon chain increases. The surfactants with tetradecanoyl and hexadecanoyl groups show a good foaming property and especially, the long-chain acyl-serine performs better. These are all related to the hydromethyl group in the serine.

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

Cosmetic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.

Cosmetic composition containing DOPA derivatives

A composition for topical application to human hair or skin contains a chemical analogue of dihydroxyphenyl alanine (DOPA). This chemical analogue can be absorbed by skin or by a hair follicle and metabolised in-vivo, thus leading to the formation of melanin in skin or to the growth of melanin-pigmented hair. Consequently the composition can give controlled skin darkening to mimic sun-induced tanning or can bring about the growth of dar hair in place of the grey or white hair.

Cosmestic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamic acid derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.

Hair growth composition containing citric acid esters

Triesters of citric acid are used for inducing, maintaining or increasing hair growth. Compositions for topical application to mammalian hair or scalp comprise an effective amount of from 1% to 99% by weight of an ester of citric acid having the structure (1): where, R1, R2 and R3 each independently represent a branched or unbranched alkyl, alkenyl, aryl, alkylaryl or arylalkyl group, each said group having from 1 to 18 carbon atoms, R4 represents -H, or a branched or unbranched saturated or unsaturated acyl, alkyl, aryl, alkylaryl or aylalkyl group having from 1 to 18 carbon atoms, in the presence of a cosmetically acceptable vehicle for the citric acid ester and in the absence of solid absorbent for the ester;, said effective amount of said ester being sufficient to increase hair growth in the rat, when said composition is applied topically thereto over a period of no more than three months, by at least 10% more than that obtainable using a control composition from which the said ester has been omitted, in accordance with the Rat Hair Growth Test.