16655-72-4

Usage

Uses

Used in Analytical Chemistry:
Alanine, 3-(trimethylsilyl)is used as a reference standard for chromatographic analysis, such as gas chromatography and liquid chromatography. Its enhanced stability and resistance to degradation make it an ideal choice for calibration and method development in these techniques.
Used in Biochemistry Research:
In biochemistry research, alanine, 3-(trimethylsilyl)serves as a building block for the synthesis of more complex molecules. Its unique chemical properties allow for the development of novel compounds with potential applications in various fields, such as drug discovery and diagnostics.
Used in Pharmaceutical Industry:
Alanine, 3-(trimethylsilyl)is utilized in the pharmaceutical industry for drug development and formulation. Its stability and versatility make it a valuable component in the design and synthesis of new drugs, as well as in the improvement of existing drug formulations.

Upstream product

• 182291-70-9 ethyl 2-amino-3-(trimethylsilyl)propionate 
• 19196-76-0 α-Acetamido-α-cyan-β-trimethyl-silylpropionsaeure-ethylester 

Relevant academic research and scientific papers

Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of D-H2NCH(CH2SiMe3)COOH and D-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: A study on C/Si/Ge bioisosterism

Two novel efficient methods for the synthesis of racemic silicon- and germanium-containing α-amino acids of the formula type rac-H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl), starting from 3,6-diethoxy-2,5-dihydropyrazine, have been developed. Racemic α-amino acids synthesized: rac-H2NCH(CH2SiMe3)COOH (rac-2), rac-H2NCH(CH2GeMe3)COOH (rac-3), rac-H2NCH(CH2SiMe2Ph)COOH (rac-4), rac-H2NCH(CH2GeMe2Ph)COOH (rac-5), and rac-H2NCH(CH2SiMe2CH=CH2)COOH (rac-6). Preparative liquid-chromatographic resolution of rac-2 and rac-3 [CHIROBIOTIC T (glycopeptide Teicoplanin covalently linked to spherical silica gel) as the stationary phase] yielded the α-amino acids (R)-2, (S)-2, (R)-3, and (S)-3. The (R)- and (S)-enantiomers of β-(trimethylsilyl)alanine [(R)- and (S)-2] and β-(trimethylgermyl)alanine [(R)- and (S)-3] are sila-analogs and germa-analogs, respectively, of the antipodes of the non-proteinogenic α-amino acid β-tert-butylalanine [(S)- and (R)-H2NCH(CH2CMe3)COOH; (S)- and (R)-1]. Starting from the N-Fmoc-protected C/Si/Ge-analogous (D-configurated) α-amino acids (R)-1, (S)-2, and (S)-3, the C/Si/Ge-analogous decapeptides 7-9 [Ac-D-Nal1-4-Cl-D-Phe2-D-Pal3-Ser 4-N-Me-Tyr5-D-Hci6-Nle7-Arg 8-Pro9-D-Me3El-Ala10-NH2 (7, El=C; 8, El=Si; 9, El=Ge)] were prepared by sequential solid-phase synthesis. The decapeptides 7-9 were studied in vitro in a functional assay using a recombinant cell line expressing the human GnRH receptor (agonist Triptorelin). Compounds 7-9 behaved as medium-potent GnRH antagonists, the antagonistic potencies of these three C/Si/Ge analogs being very similar.