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DL-7-Azatryptophan Monohydrate

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DL-7-Azatryptophan Monohydrate Basic information
Product Name:DL-7-Azatryptophan Monohydrate
Synonyms:2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid, 3-(2-Amino-2-carboxyethyl)-1H-pyrrolo[2,3-b]pyridine;2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl);3-(2,2-Diaminoethyl)-1H-indole-7-carboxylic acid hydrate;DL-7-AZATRYPTOPHAN;TIMTEC-BB SBB005480;DL-7-AZATRYPTOPHANE extrapure;7-Aza-DL-tryptophan;1H-Pyrrolo[2,3-b]pyridine-3-alanine
CAS:7303-50-6
MF:C10H11N3O2
MW:205.21
EINECS:
Product Categories:amino;Indole Derivatives;A - H;Amino Acids;Modified Amino Acids;Fluorescent Labels & Indicators;Amino Acids & Derivatives;Amino Acids 13C, 2H, 15N;Peptide
Mol File:7303-50-6.mol
DL-7-Azatryptophan Monohydrate Structure
DL-7-Azatryptophan Monohydrate Chemical Properties
Melting point 275°C dec.
Boiling point 540.2±50.0 °C(Predicted)
density 1.49±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Store in freezer, under -20°C
pka2.20±0.10(Predicted)
form Crystalline Powder
color Slightly off-white
Optical Rotation0.0848°(C=1.0029g/100ml 1N HCL)
Major Applicationpeptide synthesis
InChI1S/C10H11N3O2/c11-8(10(14)15)4-6-5-13-9-7(6)2-1-3-12-9/h1-3,5,8H,4,11H2,(H,12,13)(H,14,15)
InChIKeySNLOIIPRZGMRAB-UHFFFAOYSA-N
SMILESNC(Cc1c[nH]c2ncccc12)C(O)=O
CAS DataBase Reference7303-50-6(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS UY8810000
Hazard Note Harmful/Store below -10C
HS Code 2933998090
Storage Class11 - Combustible Solids
MSDS Information
DL-7-Azatryptophan Monohydrate Usage And Synthesis
Chemical PropertiesWhite Powder
UsesDL-7-Azatryptophan is an unusual alpha-amino acid with a very potent fluorescent activity. Its used as a vehicle for probing the structure and dynamics of protein and peptides
Synthesis
Ethyl α-Acetamido-α-carbethoxy-β-(7-aza-3-indolyl)propionate

211179-97-4

DL-7-Azatryptophan Monohydrate

7303-50-6

Step 2: Diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate (3.5 g, 10.08 mmol) was mixed with 37% hydrochloric acid (30 mL) and the reaction was carried out at reflux for 15 hrs. Upon completion of the reaction, the mixture was concentrated to about 10 mL. acetonitrile (5 mL) was added to the concentrate and subsequently lyophilized to give an off-white solid product. The solid was redissolved in 15% aqueous ammonia solution, pH adjusted to 7, and then diluted with water (20 mL). The precipitated white solid was collected by filtration, washed sequentially with water and ethanol, and dried to give 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (1.5 g, 72.5% yield) as a white solid. The product was analyzed by LCMS (condition A): retention time = 0.29 min; ESI-MS (+) m/z 206.0 ([M+H]+).

References[1] Patent: WO2016/39749, A1. Location in patent: Page/Page column 190
[1] Patent: , 2016, . Location in patent: Page/Page column 190
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 457,458, 6554, 6555
DL-7-Azatryptophan Monohydrate Preparation Products And Raw materials
Raw materialsEthyl α-Acetamido-α-carbethoxy-β-(7-aza-3-indolyl)propionate-->Water-->Hydrochloric acid
Preparation Products2-(2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraen-7-yl)ethanamine
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