43189-45-3

Basic information

• Product Name: (R)-2-THIENYLGLYCINE
• Synonyms: (R)-AMINO-THIOPHEN-2-YL-ACETIC ACID;(R)-2-THIENYLGLYCINE;(S)-2-THIENYLGLYCINE;(S)-AMINO-THIOPHEN-2-YL-ACETIC ACID;D-2-THIENYLGLYCINE;D-2-(2-THIENYL)-GLYCINE;D-ALPHA-(2-THIENYL)GLYCINE;H-D-THG-OH
• CAS NO: 43189-45-3
• Molecular Formula: C₆H₇NO₂S
• Molecular Weight: 157.19
• EINECS: 256-134-7
• Product Categories: Unusual amino acids;pharmacetical;Amino Acids;I - Z;Modified Amino Acids
• Mol File: 43189-45-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 189℃
• Boiling Point: 311.8 °C at 760 mmHg
• Flash Point: 142.4 °C
• Appearance: /
• Density: 1.418
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.88±0.10(Predicted)
• CAS DataBase Reference: (R)-2-THIENYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-THIENYLGLYCINE(43189-45-3)
• EPA Substance Registry System: (R)-2-THIENYLGLYCINE(43189-45-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 43189-45-3(Hazardous Substances Data)

Usage

Description

(R)-2-Thienylglycine, also known as (R)-2-(Thiophen-2-yl)glycine, is an optically active amino acid derivative featuring a thienyl group attached to the alpha carbon of glycine. It is a white powder and is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
(R)-2-Thienylglycine is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with chiral centers. Its optical activity makes it a valuable building block for the development of enantiomerically pure drugs, which can have significant implications in terms of efficacy and safety.
Used in Chemical Synthesis:
(R)-2-Thienylglycine is used as a key component in the one-pot regioselective synthesis of substituted arylglycines. This process is facilitated by penicillin G acylase, an enzyme that catalyzes the kinetic resolution of racemic mixtures, allowing for the production of enantiomerically pure arylglycines with high selectivity.
Used in Enzyme Research:
The unique structure of (R)-2-Thienylglycine makes it an interesting substrate for studying the activity and selectivity of enzymes, such as penicillin G acylase. This can provide valuable insights into enzyme mechanisms and help in the design of more efficient biocatalysts for industrial applications.
Used in Material Science:
The thienyl group in (R)-2-Thienylglycine can potentially be utilized in the development of novel materials with specific properties, such as conductivity or photoluminescence. This application is still in the exploratory stage, but the unique chemical properties of (R)-2-Thienylglycine make it a promising candidate for further research in this field.

Upstream product

• 97036-25-4 (2S)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 98-03-3 thiophene-2-carbaldehyde 
• 97036-29-8 (2S)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(2-thienyl)essigsaeure 
• 97036-27-6 (2R)-(+)-2-<(4S,5S)-(2,2-Dimethyl-4-phenyl-1,3-dioxan-5-yl)amino>-2-(2-thienyl)acetonitril 
• 97036-23-2 (4S,5S)-(+)-2,2-Dimethyl-4-phenyl-5-<(2-thienylmethylen)amino>-1,3-dioxan 
• 97101-15-0 (2R)-(-)-2-<(1S,2S)-(2-Hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-2-(2-thienyl)essigsaeure 
• 1355742-75-4 (S)-2-benzyloxycarbonylamino-2-(thiophen-2-yl)-acetonitrile 
• 21124-40-3 D,L-(2-thienyl)glycine 
• 110728-00-2 C₁₄H₁₃NO₃S 
• 145057-92-7 (R)-2-<(2-hydroxy-1-phenylethyl)amino>-2-(2-thienyl)ethanenitrile 
• 145058-07-7 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(2-thienyl)ethanoate 
• 145057-99-4 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(2-thienyl)ethanoic acid 
• 74126-04-8 DL-5-(2-thienyl)hydantoin 
• 65700-48-3 N-carbamyl-D-(-)2-thienylglycine 

Downstream Products

• 1391629-03-0 (3S,6R)-4-(5-(4-fluorophenyl)isoxazole-3-carbonyl)-3-isobutyl-6-(thiophen-2-yl)piperazin-2-one 
• 171661-56-6 2-amino-2-(thiophen-2-yl)ethan-1-ol 
• 208259-66-9 Fmoc-Tgly-OH 

Relevant articles and documents

Enantioselective hydrocyanation of N-protected aldimines

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly]2[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly]2[(S)-binap]}]Cl affords the amino nitriles in 92 - 99% ee. The reaction is carried out in tert-C 4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500 - 5000 at -20 to 0°C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase

Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an in-expensive route to a large variety of N-phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5 °C in acetic acid/HCl, this simple one-pot operation resulted in the formation of single regioisomers only (≥98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH 8.0 occurred generally with E values >100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)- and (R)-antipodes of non-natural α-amino acids in small-to large-scale quantities.

An Efficient and Practical Synthesis of L-α-Amino Acids Using (R)-Phenylglycinol as a Chiral Auxiliary

L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide.The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.