(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid - 479064-99-8

(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid

Catalog Number: EVT-339065
CAS Number: 479064-99-8
Molecular Formula: C25H23NO4
Molecular Weight: 401.5 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid, also known as Fmoc-L-3-(p-Tolyl)alanine, is a derivative of the amino acid alanine. It is commonly used in peptide synthesis as a protecting group for the N-terminal amino group. This paper will discuss the method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges of Fmoc-L-3-(p-Tolyl)alanine.
Applications in Various Fields
In medical research, (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine plays a role in drug development as a protecting group for the N-terminal amino group in peptide synthesis. It has also been used in clinical trials as a component of peptides with antimicrobial and anticancer activity. Benefits of using (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine in peptide synthesis include increased stability and solubility of the peptide.
In environmental research, (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine may have effects on ecosystems and play a role in pollution management. However, there is limited research on these topics.
In industrial research, (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations include the use of hazardous chemicals and the generation of waste.

Properties

CAS Number

479064-99-8

Product Name

(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid

IUPAC Name

(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid

Molecular Formula

C25H23NO4

Molecular Weight

401.5 g/mol

InChI

InChI=1S/C25H23NO4/c1-16-10-12-17(13-11-16)23(14-24(27)28)26-25(29)30-15-22-20-8-4-2-6-18(20)19-7-3-5-9-21(19)22/h2-13,22-23H,14-15H2,1H3,(H,26,29)(H,27,28)/t23-/m0/s1

InChI Key

QVNBKPSESKXKBL-QHCPKHFHSA-N

SMILES

CC1=CC=C(C=C1)C(CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Canonical SMILES

CC1=CC=C(C=C1)C(CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Isomeric SMILES

CC1=CC=C(C=C1)[C@H](CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
Method of Synthesis or Extraction
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine can be synthesized using various methods, including solid-phase peptide synthesis, solution-phase peptide synthesis, and enzymatic synthesis. Solid-phase peptide synthesis is the most commonly used method for synthesizing (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine. This method involves the stepwise addition of protected amino acids to a solid support, followed by deprotection and cleavage of the peptide from the support. Solution-phase peptide synthesis involves the same steps but is carried out in solution rather than on a solid support. Enzymatic synthesis involves the use of enzymes to catalyze the formation of peptide bonds.
The efficiency and yield of each method vary depending on the specific conditions used. Solid-phase peptide synthesis is generally considered the most efficient method, with yields of up to 95%. Solution-phase peptide synthesis and enzymatic synthesis typically have lower yields, ranging from 50% to 80%. Environmental and safety considerations for each method include the use of hazardous chemicals, such as organic solvents and acids, and the generation of waste.
Chemical Structure and Biological Activity
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine has a chemical structure consisting of a fluorenylmethoxycarbonyl (Fmoc) protecting group attached to the N-terminal amino group of L-3-(p-Tolyl)alanine. The Fmoc group can be removed using a base, such as piperidine, to expose the amino group for further peptide synthesis.
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine has been shown to have biological activity as a modulator of the GABA(A) receptor. It has also been used in the synthesis of peptides with antimicrobial and anticancer activity.
Biological Effects
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine has been shown to have effects on cell function and signal transduction through its modulation of the GABA(A) receptor. It has also been shown to have potential therapeutic effects as a component of peptides with antimicrobial and anticancer activity.
However, (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine may also have potential toxic effects, as it has been shown to induce apoptosis in certain cell types.
Future Perspectives and Challenges
Current limitations in the use and study of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine include the potential toxic effects and limited research on its environmental effects. Possible solutions and improvements include the development of alternative protecting groups for the N-terminal amino group in peptide synthesis and further research on the environmental impact of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine.
Future trends and prospects in the application of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine in scientific research include the development of peptides with novel biological activity and the use of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(p-tolyl)propanoic acid(p-Tolyl)alanine in the synthesis of peptide-based materials for biomedical applications.

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