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Home > Encyclopedia > 2-Chloro-L-phenylalanine

2-Chloro-L-phenylalanine

2-Chloro-L-phenylalanine structure

2-Chloro-L-phenylalanine 

structure
  • CAS No:

    103616-89-3

  • Formula:

    C9H10ClNO2

  • Chemical Name:

    2-Chloro-L-phenylalanine

  • Synonyms:

    L-Phenylalanine,2-chloro-;2-Chloro-L-phenylalanine;o-Chloro-L-phenylalanine;L-o-Chlorophenylalanine;L-2-Chlorophenylalanine;(2S)-2-Amino-3-(2-chlorophenyl)propanoic acid;(S)-2-Amino-3-(2-chlorophenyl)propanoicacid

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

2-Chloro-L-phenylalanine is a phenylalanine derivative.

2-Chloro-L-phenylalanine Basic Attributes

199.63

199.63

DTXSID90375799

29224999

Characteristics

63.3

-0.8

1.336±0.06 g/cm3(Predicted)

233-235°C

339.5±32.0 °C(Predicted)

159.1±25.1 °C

1.590

Insoluble in water.

−20°C

148.86 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]

Safety Information

3

24/25

Xi

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

2-Chloro-L-phenylalanine Use and Manufacturing

The PAL gene of R. glutinis was synthesized by Genscript Corporation, Scotch Plains, USA according to the protein sequence of the PAL of Rhodosporidium toruloides ATCC 10788 which sequence is listed in the protein database of the NCBI under number CAA31209. The codons of the synthetic PAL gene were optimised for expression in E. coli. The synthesized gene was ligated in the Smal site of pUC57 by Genscript to give the pUC57_PAL construct. The lyophilized plasmid (5 μg) (obtained from Genscript) was dissolved in 50 μl MilliQ water and 1 μl of this solution was used to transform an aliquot of E. coli DH5α chemicallly competent cells (Invitrogen, Breda, The Netherlands) according to the protocol of the supplier. After overnight growth on solid LB medium (10 g/l Bacto Trypton (Difco, Becton, Dickinson and Company, Sparks, MD, USA), 5 g/l Bacto Yeast Extract (Difco) and 5 g/ I sodium chloride (Merck, Darmstadt, Germany) supplemented with 100 μg/ml Carbenicillin (Sigma, St. Louis, MO, USA), at 37 °C, one colony was transferred to 20 ml liquid LB medium containing 100 μg/ml carbenicillin. Glycerol stocks (8percent final concentration glycerol) of this culture were prepared and stored at -80 °C. E. coli DH5α containing the pUC57_PAL construct as obtained above was inoculated in1000 ml LB medium supplemented with 100 μg/ml Carbenicillin and grown overnight at 28 °C. This culture was used to inoculate 10 liter TB medium (12 g/I Bacto Trypton, 24 g/I Bacto Yeast Extract, 2.31 g/l KHStep (N):; Preparation of (S)-2-amino-3-(2-chloro-phenyD-propionic acid; The PAL gene of R. glutinis was synthesized by Genscript Corporation, Scotch Plains, USA according to the protein sequence of the PAL of Rhodosporidium toruloides ATCC 10788 which sequence is listed in the protein database of the NCBI under number CAA31209. The codons of the synthetic PAL gene were optimised for expression in E. coli. The synthesized gene was ligated in the Sma\ site of pUC57 by Genscript to give the pUC57_PAL construct. The lyophilized plasmid (5 μg) (obtained from Genscript) was dissolved in 50 μl MiIIiQ water and 1 μl of this solution was used to transform an aliquot of E. coli DH5α chemicallly competent cells (Invitrogen, Breda, The Netherlands) according to the protocol of the supplier. After overnight growth on solid LB medium (10 g/l Bacto Trypton (Difco, Becton, Dickinson and Company, Sparks, MD, USA), 5 g/l Bacto Yeast Extract (Difco) and 5 g/ I sodium chloride (Merck, Darmstadt, Germany) supplemented with 100 μg/ml Carbenicillin (Sigma, St. Louis, MO, USA), at 37 A solution of 2-nitrobenzenesulfonyl chloride (6.7 g) in tetrahydrofuran (50 mL) was added dropwise for 30 minutes to a mixture of Thionyl chloride (2 mL, 27.42 mmol) was added dropwise to anhydrous methanol(7.5 mL) cooled to ooc under nitrogen. After stirring for 5 minutes,

Computed Properties

Molecular Weight:199.63
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:199.0400063
Monoisotopic Mass:199.0400063
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:187
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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