6-CHLORO-L-TRYPTOPHAN
- Product Name
- 6-CHLORO-L-TRYPTOPHAN
- CAS No.
- 33468-35-8
- Chemical Name
- 6-CHLORO-L-TRYPTOPHAN
- Synonyms
- H-6-Cl-Trp-OH;6-Chlo-L-Tryptophan;L-6-CHLOROTRYPTOPHAN;6-CHLORO-L-TRYPTOPHAN;Tryptophan Impurity 14;Tryptophan Impurity 30;6-Chloro-(s)-Tryptophan;6-Chloro-L-tryptophane ;L-Tryptophan, 6-chloro-;6-CHLORO-L-TRYPTOPHAN USP/EP/BP
- CBNumber
- CB0399395
- Molecular Formula
- C11H11ClN2O2
- Formula Weight
- 238.67
- MOL File
- 33468-35-8.mol
6-CHLORO-L-TRYPTOPHAN Property
- Melting point:
- 244-246°C
- Boiling point:
- 476.9±45.0 °C(Predicted)
- Density
- 1.474±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,2-8°C
- solubility
- Aqueous Acid (Slightly), Methanol (Very Slightly, Heated)
- form
- Solid
- pka
- 2.22±0.10(Predicted)
- color
- Off-White to Pale Beige
- InChI
- InChI=1S/C11H11ClN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1
- InChIKey
- FICLVQOYKYBXFN-VIFPVBQESA-N
- SMILES
- C(O)(=O)[C@H](CC1C2=C(C=C(Cl)C=C2)NC=1)N
- CAS DataBase Reference
- 33468-35-8
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- C423210
- Product name
- 6-ChloroL-Tryptophan
- Packaging
- 10mg
- Price
- $95
- Updated
- 2021/12/16
- Product number
- C5034-42
- Product name
- 6-Chloro-L-tryptophan
- Packaging
- 10mg
- Price
- $355
- Updated
- 2021/12/16
- Product number
- 268109
- Product name
- 6-Chloro L-tryptophan
- Packaging
- 50mg
- Price
- $446
- Updated
- 2021/12/16
- Product number
- C423210
- Product name
- 6-ChloroL-Tryptophan
- Packaging
- 500mg
- Price
- $755
- Updated
- 2021/12/16
- Product number
- 8474
- Product name
- 6-Chloro-L-tryptophan
- Purity
- 98%
- Packaging
- 100mg
- Price
- $890
- Updated
- 2021/12/16
6-CHLORO-L-TRYPTOPHAN Chemical Properties,Usage,Production
Chemical Properties
Colourless Prisms
Uses
The natural enantiomer of Chlorotryptophan.
Definition
ChEBI: 6-chloro-L-tryptophan is a non-proteinogenic L-alpha-amino acid that is L-tryptophan in which the hydrogen at position 6 on the indole ring has been replaced by a chlorine. It is a non-proteinogenic L-alpha-amino acid, a L-tryptophan derivative and an organochlorine compound. It is a tautomer of a 6-chloro-L-tryptophan zwitterion.
Synthesis
50517-10-7
33468-35-8
The general procedure for the synthesis of (S)-2-amino-3-(6-chloro-1H-indol-3-yl)propionic acid from AC-DL-6-chlorotryptophan was as follows: 1. 6-Chloroindole (500 mg, 3.31 mmol, 1 eq.) and L-serine (695 mg, 6.62 mmol, 2 eq.) were dissolved in acetic acid (10 mL) and acetic anhydride (3.1 mL, 33.1 mmol, 10 eq.) was added. The mixture was stirred at 73 °C for 4 hours under argon protection. Upon completion of the reaction, the mixture was concentrated to half the original volume, diluted with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, dried over sodium sulfate and evaporated to give the crude product N-acetyl-6-chloro-D,L-tryptophan (686 mg, 74% yield). 2. N-Acetyl-6-chloro-D,L-tryptophan (686 mg, 1.45 mmol) was dissolved in pH 8.0 phosphate buffer (50 mL) containing 1 mM CoCl2-6H2O. Acylase I (500 mg) was added and stirred at 37 °C for 24 h, during which time the pH was adjusted with LiOH to 8.0. Upon completion of the reaction, the mixture was heated to 60 °C and kept at 60 °C for 5 min, cooled to room temperature and then filtered through diatomaceous earth. The filtrate was acidified with HCl to pH about 3 and extracted with EtOAc. The aqueous layer was lyophilized and used as crude product for the next reaction (estimated yield 43%, based on the theoretical yield of L-enantiomer, 125.4 mg). 3. 6-Chloro-L-tryptophan (125.4 mg, 0.527 mmol, 1 eq.) was dissolved in a water/acetone (1:1, v/v) solvent mixture and NaHCO3 (88.5 mg, 1.05 mmol, 2 eq.) was added. Fmoc-OSu (195.6 mg, 0.58 mmol, 1.1 eq.) was dissolved in acetone and added to the reaction mixture in batches over 3 hours. After completion of the reaction, the acetone was evaporated and the aqueous layer was acidified with acetic acid to pH about 3 and extracted with EtOAc. The organic layers were combined, dried over sodium sulfate and evaporated. The crude product was purified by fast column chromatography (eluent: hexane:EtOAc:AcOH = 10:9:1) to give pure Fmoc-6-chloro-L-tryptophan (237 mg, 98% yield).
References
[1] Patent: WO2015/153761, 2015, A2. Location in patent: Paragraph 00256
6-CHLORO-L-TRYPTOPHAN Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-CHLORO-L-TRYPTOPHAN manufacturers
- Product
- 6-CHLORO-L-TRYPTOPHAN 33468-35-8
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2018-12-22