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2935-35-5

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2935-35-5 Usage

Chemical Properties

White crystalline powder

Uses

L-(+)-2-Phenylglycine is a derivative of Glycine (G615990), the smallest of all the amino acids, and is also used to treat schizophrenia, stroke, and benign prostatic hyperplasia. L-(+)-2-Phenylglycine is also used as an N-linked side chain of an SMTP (Stachybotrys microspora tripenyl phenols) congener, which was potent in enhancing plasminogen activation in S. microspora.

Definition

ChEBI: The S stereoisomer of alpha-phenylglycine.

Purification Methods

Crystallise it from EtOH. [Kaneko J Chem Soc Jpn 60 538 1939, Rudman et al. J Am Chem Soc 74 551 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2694-2697 1961, Beilstein 14 III 1187, 14 IV 1317.]

Check Digit Verification of cas no

The CAS Registry Mumber 2935-35-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,9,3 and 5 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2935-35:
(6*2)+(5*9)+(4*3)+(3*5)+(2*3)+(1*5)=95
95 % 10 = 5
So 2935-35-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)

2935-35-5 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
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  • TCI America

  • (P1288)  L-2-Phenylglycine  >98.0%(HPLC)(T)

  • 2935-35-5

  • 25g

  • 240.00CNY

  • Detail
  • TCI America

  • (P1288)  L-2-Phenylglycine  >98.0%(HPLC)(T)

  • 2935-35-5

  • 100g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (A19360)  L-(+)-2-Phenylglycine, 98+%   

  • 2935-35-5

  • 25g

  • 287.0CNY

  • Detail
  • Alfa Aesar

  • (A19360)  L-(+)-2-Phenylglycine, 98+%   

  • 2935-35-5

  • 100g

  • 913.0CNY

  • Detail
  • Alfa Aesar

  • (A19360)  L-(+)-2-Phenylglycine, 98+%   

  • 2935-35-5

  • 500g

  • 2937.0CNY

  • Detail
  • Aldrich

  • (237647)  L−(+)-α-Phenylglycine  99%

  • 2935-35-5

  • 237647-25G

  • 370.89CNY

  • Detail
  • Aldrich

  • (237647)  L−(+)-α-Phenylglycine  99%

  • 2935-35-5

  • 237647-100G

  • 1,175.85CNY

  • Detail

2935-35-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name L-α-phenylglycine

1.2 Other means of identification

Product number -
Other names L-alpha-phenylglycine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2935-35-5 SDS

2935-35-5Relevant articles and documents

Highly stereoselective recognition and deracemization of amino acids by supramolecular self-assembly

So, Soon Mog,Moozeh, Kimia,Lough, Alan J.,Chin, Jik

, p. 829 - 832 (2014)

The highly stereoselective supramolecular self-assembly of α-amino acids with a chiral aldehyde derived from binol and a chiral guanidine derived from diphenylethylenediamine (dpen) to form the imino acid salt is reported. This system can be used to cleanly convert D-amino acids into L-amino acids or vice versa at ambient temperature. It can also be used to synthesize α-deuterated D- or L-amino acids. A crystal structure of the ternary complex together with DFT computation provided detailed insight into the origin of the stereoselective recognition of amino acids. A communal effort: A chiral guanidine derivative 1 and a chiral aldehyde 2 underwent self-assembly with amino acids to promote inversion of the stereogenic center of the guest (see scheme). The supramolecular self-assembly exhibited high stereoselectivity for amino acid recognition and was found to be useful for the separation of racemic mixtures of amino acids as well as for their deracemization. Copyright

Stereoselective hydration of (RS)-phenylglycine nitrile by new whole cell biocatalysts

Hensel, Martina,Lutz-Wahl, Sabine,Fischer, Lutz

, p. 2629 - 2633 (2002)

Five new bacterial isolates with stereoselective nitrile hydratase activity against (RS)-2-phenylpropionitrile and (RS)-phenylglycine nitrile were investigated. The permeabilized whole cell isolates selectively hydrate the (S)-enantiomer of phenylglycine nitrile with E values of 1.2-5.4. One isolate, which was identified as Pantoea endophytica, produced pure (S)-phenylglycine (>99% ee) as a result of hydrolysis of (S)-phenylglycine amide by an (S)-specific amidase. Surprisingly, in the hydrolysis of (RS)-phenylglycine nitrile, it was found that the (R)-amide was accumulated in excess (21% ee) despite the nitrile hydratase produced by Pantoea endophytica was (S)-selective. The synthesis of pure (R)-phenylglycine (>99% ee) was achieved in time course studies using another Pantoea sp. with (R)-selective amidase. In the case of Nocardioides sp. the intermediate product, (S)-phenylglycine amide, could be produced (52% ee) without its subsequent hydrolysis into the acid due to the apparent absence of any amidase activity.

Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography

Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong

supporting information, p. 390 - 398 (2021/01/13)

Separation of racemic mixtures is of great importance and interest in chemistry and pharmacology. Porous materials including metal-organic frameworks (MOFs) have been widely explored as chiral stationary phases (CSPs) in chiral resolution. However, it remains a challenge to develop new CSPs for reversed-phase high-performance liquid chromatography (RP-HPLC), which is the most popular chromatographic mode and accounts for over 90% of all separations. Here we demonstrated for the first time that highly stable Zr-based MOFs can be efficient CSPs for RP-HPLC. By elaborately designing and synthesizing three tetracarboxylate ligands of enantiopure 1,1′-biphenyl-20-crown-6, we prepared three chiral porous Zr(IV)-MOFs with the framework formula [Zr6O4(OH)8(H2O)4(L)2]. They share the same flu topological structure but channels of different sizes and display excellent tolerance to water, acid, and base. Chiral crown ether moieties are periodically aligned within the framework channels, allowing for stereoselective recognition of guest molecules via supramolecular interactions. Under acidic aqueous eluent conditions, the Zr-MOF-packed HPLC columns provide high resolution, selectivity, and durability for the separation of a variety of model racemates, including unprotected and protected amino acids and N-containing drugs, which are comparable to or even superior to several commercial chiral columns for HPLC separation. DFT calculations suggest that the Zr-MOF provides a confined microenvironment for chiral crown ethers that dictates the separation selectivity.

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

Coady, Tracey M.,Coffey, Lee,Kinsella, Michael,Lennon, Claire M.,Mareya, Tatenda M.,O'Reilly, Catherine

, p. 512 - 520 (2020/10/02)

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

Ultrasound-Controlled Chiral Separation of Four Amino Acids and 2,2,2-Trifluoro-1-(9-anthryl)ethanol

Lee, Jae Hwan,Ryoo, Jae Jeong

, p. 146 - 149 (2019/02/07)

Chiral separation of 4-hydroxyphenylglycine, phenylglycine, tryptophan, methionine, and 2,2,2-trifluoro-1-(9-anthryl)ethanol (TFAE) was performed under ultrasound reduction at room temperature and high temperature (50 °C). At high temperature (50 °C), both α and Rs were improved slightly under ultrasound reduction as compared to those under non-ultrasonic and ultrasonic irradiation (50 watt/L) conditions. Even at low temperatures, the largest α was observed under ultrasound reduction conditions, except in the case of methionine. However, at low temperature, Rs was reduced under ultrasound (50 watt/L) irradiation, but was improved under ultrasound reduction rather than under the continuous ultrasonic irradiation. Similar to the fact that gradient elution (based on solvent polarity) can improve α, ultrasound reduction can improve α and Rs. Ultrasound reduction is demonstrated to aid the rapid separation of chiral compounds with improved resolution, especially, at high temperatures. Although chromatographic separation using ultrasound has been rarely dealt with until now, ultrasound can be used as an external field in chromatography.

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