(2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

Base Information

• Chemical Name: (2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate
• CAS No.: 153-94-6
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.228
• Hs Code.: 29339990
• Mol file: 153-94-6.mol

Synonyms:(2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;(2R)-2-ammonio-3-(1H-indol-3-yl)propanoate;D-tryptophan zwitterion;CHEBI:57719;A809480

Chemical Property of (2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

Chemical Property:

• Appearance/Colour: White or yellow crystalline powder
• Vapor Pressure: 4.27E-07mmHg at 25°C
• Melting Point: 282-285 °C
• Refractive Index: 31 ° (C=1, H2O)
• Boiling Point: 447.9 °C at 760 mmHg
• PKA: 2.30±0.10(Predicted)
• Flash Point: 224.7 °C
• PSA: 79.11000
• Density: 1.362 g/cm³
• LogP: 1.82260
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
• Water Solubility.: 11 g/L (20 ºC)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99.00% ^*data from raw suppliers

D-Tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 24/25-36/37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@H](C(=O)[O-])[NH3+]
• Description: D(+)-tryptophan is the D-form (non-proteinogenic form) of the amino acid tryptophan. It can be used for Human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. It is also a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners. D-tryptophan (Full name D (+)-Tryptophan) is a white to pale yellow or white crystalline powder at room temperature, odorless or slight odor, slightly sweet taste. Solubility in water is 1.14 g (25 ℃), soluble in dilute acid and alkali, stable in alkali, decomposed in strong acid, slightly soluble in ethanol, not soluble in chloroform, ethyl ether. It plays an important role for human and animal growth and development, metabolism, known as the second essential amino acids. They are almost identical with L-type and physical and chemical properties, and only the optical activity is opposite. But their distribution, function and coenzyme have diversity. Its melting point is very high, generally above 200 degrees. It can dissolve in water, and in the near UV region it has the ability to absorb light. Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG. the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan). The distinguishing structural characteristic of tryptophan is that it contains an indole functional group. It is an essential amino acid as defined by its growth effects on rats.
• Uses: An essential amino acid found in naturally produced pedtides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins. An essential amino acid found in naturally produced peptides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins. D-Tryptophan is used for human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. The product is a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners.

Technology Process of (2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate

There total 47 articles about (2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

C15H15N3*C18H14Cl2N2O3 → D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With benzylamine hydrochloride; In water; isopropyl alcohol; at 20 ℃; for 1h;

DOI:10.1002/anie.201914797

Reference yield: 69.0%

indole (120-72-9) + L-serin (56-45-1,83245-15-2) → D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

indole; L-serin; With Salmonella enterica tryptophan synthase; In methanol; aq. phosphate buffer; at 37 ℃; pH=8.0; Enzymatic reaction;

With (2R)-aspartic acid; In methanol; aq. phosphate buffer; pH=8.0;

In aq. phosphate buffer; deuteromethanol; at 37 ℃; pH=8.0; stereoselective reaction; Enzymatic reaction;

DOI:10.1021/acscatal.9b00739

Reference yield: 48.0%

Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol; In water; at 30 ℃; for 8h; pH=7.3; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.08.111

upstream raw materials:

D-Tryptophan methyl ester

N-acetyl-D-tryptophan

N^α-chloroacetyl-D-tryptophan

N-(benzyloxycarbonyl)-D-tryptophan

Downstream raw materials:

N-Cbz-D-Phe-L-Trp-OH

carbobenzyloxy-L-trytophan

N-(tert-Butyloxycarbonyl)-L-tryptophan

oxindolyl-L-alanine

Refernces

• 1、 Verkuijl, Bastiaan J. V.,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.. "Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes". . p. 6526 - 6533. Retrieved 2009.
• 2、 Akhtar, M. Kalim,Campopiano, Dominic J.,De Cesare, Silvia,Loake, Gary J.,Marles-Wright, Jon,Serpico, Annabel. "D-Phenylglycine aminotransferase (d-PhgAT)-substrate scope and structural insights of a stereo-inverting biocatalyst used in the preparation of aromatic amino acids". . p. 6533 - 6543. Retrieved 2020.
• 3、 Brenner et al.. "-". . p. 1908,1910. Retrieved 1948.
• 4、 Lee, Jae Hwan,Ryoo, Jae Jeong. "Ultrasound-Controlled Chiral Separation of Four Amino Acids and 2,2,2-Trifluoro-1-(9-anthryl)ethanol". . p. 146 - 149. Retrieved 2019.
• 5、 Song, Ya-Ya,Song, Xiao-Dong,Yuan, Heng,Cheng, Chang-Jing. "Thermo-responsive adsorption and separation of amino acid enantiomers using smart polymer-brush-modified magnetic nanoparticles". . p. 3194 - 3207. Retrieved 2016.
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• 7、 Qing, Haiqun,Jiang, Xinyu,Yu, Jingang. "Separation of tryptophan enantiomers by ligand-exchange chromatography with novel chiral ionic liquids ligand". . p. 160 - 165. Retrieved 2014.
• 8、 Clapp, Charles H.,Pachuski, Justin,Bassett, Natasha F.,Bishop, Kathleen A.,Carter, Gillian,Young, Megan,Young, Thomas,Fu, Yuhan. "N-linoleoylamino acids as chiral probes of substrate binding by soybean lipoxygenase-1". . p. 170 - 177. Retrieved 2018.
• 9、 Yang, Yi,Wu, Jingwei,Su, Ping,Yang, Ye,Huang, Jun,Wang, Yingying. "Immobilization of HSA on polyamidoamine-dendronized magnetic microspheres for application in direct chiral separation of racemates". . p. 775 - 782. Retrieved 2014.
• 10、 Reubsaet,Beijnen,Bult,Hop,Vermaas,Kellekule,Kettenes-Van Den Bosch,Underberg. "Structural identification of the degradation products of the antitumor peptide antagonist [Arg6, D-Trp7,9, MePhe8]substance P (6-11)". . p. 4431 - 4436. Retrieved 1995.