acetyl-laevo-tryptophan

laevo-2-acetamido-3-(1H-indol-3-yl)propanoic acid

CAS: 1218-34-4 C13 H14 N2 O3 MW: 246.26618000

Identification

Nameacetyl-laevo-tryptophan
IUPAC2-acetamido-3-(1H-indol-3-yl)propanoic acid
CAS Number1218-34-4
EINECS214-935-9
FDA UNIIU9264T8OAE
Molecular FormulaC13 H14 N2 O3
Molecular Weight246.26618000
MDL NumberMFCD00065976
Nikkaji NumberJ61.737G
XlogP31.10 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 586.00 to 587.00 °C. @ 760.00 mm Hg (est)
Flash Point 587.00 °F. TCC ( 308.60 °C. ) (est)
logP (o/w) 0.702 (est)
Shelf Life 12.00 month(s) or longer if stored properly.
Storage refrigerate in tightly sealed containers.
Soluble in water, 2512 mg/L @ 25 °C (est)
Similar Items note

No sensory data available

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 3580 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorydietary supplements
Recommendation for acetyl-laevo-tryptophan usage levels up tonot for fragrance use.
Recommendation for acetyl-laevo-tryptophan flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

AC-Try (2S)-2- acetamido-3-(1H-indol-3-yl)propanoic acid L-2- acetamido-3-(1H-indol-3-yl)propanoic acid laevo-2- acetamido-3-(1H-indol-3-yl)propanoic acid acetyl-L-trp acetyl-L-tryptophan N- acetyl-L-tryptophan N- acetyl-laevo-tryptophan (S)-N- acetyltryptophan L- tryptophan, N-acetyl- tryptophan, N-acetyl-, L- PubMed: N-acetyl-L-tryptophan, a substance-P receptor antagonist attenuates aluminum-induced spatial memory deficit in rats PubMed: Protective role of N-acetyl-l-tryptophan against hepatic ischemia-reperfusion injury via the RIP2/caspase-1/IL-1? signaling pathway PubMed: N-acetyl-l-tryptophan, but not N-acetyl-d-tryptophan, rescues neuronal cell death in models of amyotrophic lateral sclerosis PubMed: Inhibition of excessive mitophagy by N-acetyl-L-tryptophan confers hepatoprotection against Ischemia-Reperfusion injury in rats PubMed: Nitration and nitrosation of N-acetyl-L-tryptophan and tryptophan residues in proteins by various reactive nitrogen species PubMed: Amelioration of ochratoxin-A induced cytotoxicity by prophylactic treatment of N-Acetyl-L-Tryptophan in human embryonic kidney cells PubMed: N-acetyl-L-tryptophan delays disease onset and extends survival in an amyotrophic lateral sclerosis transgenic mouse model PubMed: The NK1 receptor antagonist N-acetyl-L-tryptophan reduces dyskinesia in a hemi-parkinsonian rodent model PubMed: Nutritive value of N-acetyl-L-tryptophan in man PubMed: N-acetyl-L-methionine is a superior protectant of human serum albumin against post-translational oxidation as compared to N-acetyl-L-tryptophan PubMed: [Evaluation of N-acetyl-L-tryptophan in long-term intravenous administration in growing rats] PubMed: 15N-CIDNP investigations during tryptophan, N-acetyl-L-tryptophan, and melatonin nitration with reactive nitrogen species PubMed: N-acetyl-l-methionine is a superior protectant of human serum albumin against photo-oxidation and reactive oxygen species compared to N-acetyl-L-tryptophan PubMed: N-acetyl tryptophan glucopyranoside (NATG) provides radioprotection to murine macrophage J774A.1 cells PubMed: Quantitative studies on the urinary excretion of indoxyl sulfate (indican) in man following administration of L-tryptophan and acetyl-L-tryptophan PubMed: A comparative study of the effect of L-tryptophan and its acetylated derivative N-acetyl-L-tryptophan on rat muricidal behavior PubMed: Nitrosation of N-terminally blocked tryptophan and tryptophan-containing peptides by peroxynitrite PubMed: Utilization of N-acetyl-L-tryptophan given intravenously to unrestrained adult rats PubMed: Evaluation of equilibrium constants for the binding of N-acetyl-L-tryptophan to monomeric and dimeric forms of alpha-chymotrypsin PubMed: Electron distributions in peptides and related molecules. 1. An experimental and theoretical study of N-acetyl-L-tryptophan methylamide PubMed: Identification of L-tryptophan derivatives with potent and selective antagonist activity at the NK1 receptor PubMed: Characterization of the interaction of N-acyl-L-tryptophan benzyl ester neurokinin antagonists with the human neurokinin-1 receptor PubMed: Structure-function studies of N-acyl derivatives of tryptophan that function as specific cholecystokinin receptor antagonists PubMed: Fluorescence kinetics of Trp-Trp dipeptide and its derivatives in water via ultrafast fluorescence spectroscopy PubMed: The reaction of dimethyl(2-hydroxy-5-nitrobenzyl)sulfonium bromide with N-acetyl-L-tryptophan amide PubMed: New tryptophanase inhibitors: towards prevention of bacterial biofilm formation PubMed: Two L-amino acid oxidase isoenzymes from Russell's viper (Daboia russelli russelli) venom with different mechanisms of inhibition by substrate analogs PubMed: Synthesis and biological evaluation of NK1 antagonists derived from L-tryptophan PubMed: The -chymotrypsin-catalyzed hydrolysis of N-acetyl-L-tryptophan p-nitrophenyl ester in dimethyl sulfoxide at subzero temperatures PubMed: Analysis of proteases involved in phagocytic activity of macrophages through the use of various amino acid esters PubMed: Quantum mechanical calculations of tryptophan and comparison with conformations in native proteins PubMed: Electrophoretic demonstration of specific enzyme-substrate complex between pepsin and serum albumin. II. Inhibition of complex formation by acetyl-L-tryptophan and fatty acids PubMed: Second derivative fluorescence spectroscopy of tryptophan in proteins PubMed: Dimerization and oxidation of tryptophan in UV-A photolysis sensitized by kynurenic acid PubMed: Enzymic properties of nitrated alpha-chymotrypsin and delta-chymotrypsin PubMed: Platelet-activating factor stimulation of rabbit platelets is blocked by serine protease inhibitor (chymotryptic protease inhibitor) PubMed: Magnesium enhances the beneficial effects of NK1 antagonist administration on blood-brain barrier permeability and motor outcome after traumatic brain injury PubMed: Preparation and identification of anti-melatonin monoclonal antibodies PubMed: Content in cell cultures of complement esterase and two further esterases mainly hydrolysing ethyl esters of acetyl-L-phenylalanine and acetyl-L-tryptophan, respectively PubMed: Methanolysis of ethyl esters of N-acetyl amino acids catalyzed by cyclosophoraoses isolated from Rhizobium meliloti PubMed: Absence of evidence for an intermediate in the deacetylation of acetylchymotrypsin PubMed: Treatment with a substance P receptor antagonist is neuroprotective in the intrastriatal 6-hydroxydopamine model of early Parkinson's disease PubMed: Solvent effects on the fluorescence quenching of tryptophan by amides via electron transfer. Experimental and computational studies PubMed: Photochemical coupling of 5-bromo-1,3-dimethyluracil and its 6-alkyl derivatives to 3-methylindole and N alpha-acetyl-L-tryptophan methyl ester PubMed: 13c NMR studies of the conformation of N-acetyl-L-tryptophan in its complex with chymotrypsin PubMed: Tachykinin NK? receptor antagonist co-administration attenuates opioid withdrawal-mediated spinal microglia and astrocyte activation PubMed: NK1 receptor antagonists and dexamethasone as anticancer agents in vitro and in a model of brain tumours secondary to breast cancer PubMed: Crystalline hemoprotein from Pseudomonas that catalyzes oxidation of side chain of tryptophan and other indole derivatives PubMed: An enzyme in mast cells with properties like chymotrypsin PubMed: Studies of the chymotrypsinogen family of proteins. XV. pH and temperature dependence of the alpha-chymotryptic hydrolysis of N-acetyl-L-tryptophan ethyl ester PubMed: Studies of the chymotrypsinogen family of proteins. XV. pH and temperature dependence of the -chymotryptic hydrolysis of N-acetyl-L-tryptophan ethyl ester PubMed: The binding of inhibitors to alpha-chymotrypsin PubMed: Studies of the chymotrypsinogen family of proteins. IX. Steady-state kinetics of the chymotryptic hydrolysis of N-acetyl-L-tryptophan ethyl ester at pH 8.0 PubMed: THE ROLE OF METHIONINE IN ALPHA-CHYMOTRYPSIN-CATALYSED REACTIONS PubMed: One-step preparation of S-nitrosated human serum albumin with high biological activities PubMed: Fourth-derivative spectrophotometry analysis of tryptophan environment in proteins. Application to melittin, cytochrome c and bacteriorhodopsin PubMed: Synthesis and in vitro activities of NK-1 antagonists derived from L-tryptophan PubMed: KINETIC EVIDENCE FOR AN ACYL-ENZYME INTERMEDIATE IN THE ALPHA-CHYMOTRYPSIN-CATALYZED HYDROLYSIS OF N-ACETYL-L-TRYPTOPHAN ETHYL ESTER PubMed: N-Nitroso products from the reaction of indoles with Angeli's salt PubMed: Tryptophan-derived NK1 antagonists: conformationally constrained heterocyclic bioisosteres of the ester linkage PubMed: Characterizing the role of the neuropeptide substance P in experimental subarachnoid hemorrhage PubMed: The difference between alpha-and delta-chymotrypsins. Preparation and alkaline pH dependence of alpha1-chymotrypsin-catalyzed hydrolysis of N-acetyl-L-tryptophan methyl ester (ATME). The involem PubMed: Alkaline pH dependence of delta-chymotrypsin-catalyzed hydrolysis of specific substrates PubMed: Changes of protein solutions during storage: a study of albumin pharmaceutical preparations PubMed: A substance P antagonist improves outcome when administered 4 h after onset of ischaemic stroke PubMed: A new approach to preparative enzymatic synthesis. Reprinted from Biotechnology and Bioengineering, Vol. XIX, No. 9, Pages 1351-1361 PubMed: Contractile responses induced by physalaemin, an analogue of substance P, in the rat esophagus PubMed: The prokinetic-like activity of ghrelin in rat isolated stomach is mediated via cholinergic and tachykininergic motor neurones PubMed: Involvement of substance P in peripheral neuropathy induced by paclitaxel but not oxaliplatin PubMed: PAR-2 modulates pepsinogen secretion from gastric-isolated chief cells PubMed: Substance P is associated with the development of brain edema and functional deficits after traumatic brain injury PubMed: The effect of an NK1 receptor antagonist on blood spinal cord barrier permeability following balloon compression-induced spinal cord injury PubMed: Substance P promotes sleep in the ventrolateral preoptic area of rats PubMed: Contributions of tryptophan side chains to the far-ultraviolet circular dichroism of proteins PubMed: Role of neurokinin 3 receptors in supraoptic vasopressin and oxytocin neurons PubMed: A substance P antagonist reduces axonal injury and improves neurologic outcome when administered up to 12 hours after traumatic brain injury PubMed: Multiresponse optimization of a UPLC method for the simultaneous determination of tryptophan and 15 tryptophan-derived compounds using a Box-Behnken design with a desirability function PubMed: Combined tissue plasminogen activator and an NK1 tachykinin receptor antagonist: an effective treatment for reperfusion injury following acute ischemic stroke in rats PubMed: Interaction of mycobacterial polymethylpolysaccharides with paranaric acid and palmitoyl-coenzyme A: structural specificity and monomeric dissociation constants PubMed: Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol PubMed: Purification of indolyl-3-alkane alpha-hydroxylase by affinity chromatography on indolyl-agarose columns PubMed: 5-(dimethylamino)naphthalene-1-sulfonic acid, a fluorescent probe of the medium chain fatty acid binding site of serum albumin PubMed: Physical and binding properties of large fragments of human serum albumin PubMed: Orientation of tryptophan-26 in coat protein subunits of the filamentous virus Ff by polarized Raman microspectroscopy PubMed: Location of the medium chain fatty acid site on human serum albumin. Residues involved and relationship to the indole site PubMed: Investigation of diffusion-limited rates of chymotrypsin reactions by viscosity variation PubMed: The location of tryptophan, N-acetyltryptophan and alpha-chymotrypsin in reverse micelles of AOT: a fluorescence study PubMed: In vitro and in vivo properties of recombinant human serum albumin from Pichia pastoris purified by a method of short processing time PubMed: Involvement of spinal neurokinin-1 receptors in the maintenance but not induction of carrageenan-induced thermal hyperalgesia in the rat PubMed: Kinetics of enzyme attack on substrates covalently attached to solid surfaces: influence of spacer chain length, immobilized substrate surface concentration and surface charge PubMed: Self-sustained pH oscillations in immobilized proteolytic enzyme systems PubMed: Indole-3-acetic acid (IAA) production by Arthrobacter species isolated from Azolla PubMed: Refined models for the preferential interactions of tryptophan with phosphocholines PubMed: Internal vibrations of a molecule consisting of rigid segments. I. Non-interacting internal vibrations PubMed: Purification, characterization and localization of serine protease of Morris hepatoma 8999 PubMed: Stimulation of airway sensory nerves by cyclosporin A and FK506 in guinea-pig isolated bronchus PubMed: Comparative studies of the specificities of -chymotrypsin and subtilisin BPN'. Studies with flexible substrates PubMed: [Stereochemistry of proton catalyzed dimerization of 3-alkyl-indoles] PubMed: Imprinting of lyophilized alpha-chymotrypsin affects the reactivity of the active-site imidazole PubMed: Stopped-flow chemical modification with N-bromosuccinimide: a good probe for changes in the microenvironment of the Trp 62 residue of chicken egg white lysozyme PubMed: Direct determination of the stoichiometry of charge transfer complexes PubMed: Interaction of specific amino acid derivatives with dimeric alpha-chymotrypsin PubMed: Kinetic behaviour of alpha-chymotrypsin in reverse micelles. A stopped-flow study