(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acid - 381241-08-3

(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acid

Catalog Number: EVT-251241
CAS Number: 381241-08-3
Molecular Formula: C22H23NO4
Molecular Weight: 365,43 g/mole
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acid, also known as Fmoc-L-2,3-diaminocyclohex-2-ene-1-carboxylic acid, is a synthetic amino acid derivative that has gained significant attention in the fields of medical, environmental, and industrial research. This paper aims to provide an overview of the synthesis, chemical structure, biological activity, and potential applications of Fmoc-L-2,3-diaminocyclohex-2-ene-1-carboxylic acid.
Applications in Various Fields
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid has various applications in medical, environmental, and industrial research. In medical research, it can be used as a building block for the synthesis of peptides and peptidomimetics with enhanced bioactivity and stability. It can also be used as a tool for studying the structure-activity relationship of peptides and their biological targets.
In environmental research, (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid can be used as a probe for studying the fate and transport of peptides in the environment. It can also be used as a tool for developing new methods for detecting and monitoring pollutants in water and soil.
In industrial research, (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid can be used in the manufacturing of pharmaceuticals, agrochemicals, and other specialty chemicals. It can also be used to improve the quality and efficiency of industrial processes, as well as to ensure the health and safety of workers and the environment.

Properties

CAS Number

381241-08-3

Product Name

(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acid

IUPAC Name

(1R,2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)cyclohexane-1-carboxylic acid

Molecular Formula

C22H23NO4

Molecular Weight

365,43 g/mole

InChI

InChI=1S/C22H23NO4/c24-21(25)18-11-5-6-12-20(18)23-22(26)27-13-19-16-9-3-1-7-14(16)15-8-2-4-10-17(15)19/h1-4,7-10,18-20H,5-6,11-13H2,(H,23,26)(H,24,25)/t18-,20-/m1/s1

SMILES

C1CCC(C(C1)C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Synonyms

Fmoc-trans-2-aminocyclohexane carboxylic acid (1R,2R+1S,2S);Fmoc-1,2-trans-ACHC (1R,2R+1S,2S)
Method of Synthesis or Extraction
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid can be synthesized using various methods, including solid-phase peptide synthesis, solution-phase peptide synthesis, and microwave-assisted synthesis. Solid-phase peptide synthesis involves the use of a resin-bound amino acid, which is coupled with the (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid derivative using a coupling reagent. Solution-phase peptide synthesis involves the use of a solution of the (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid derivative, which is coupled with the amino acid using a coupling reagent. Microwave-assisted synthesis involves the use of microwave irradiation to accelerate the coupling reaction.
The efficiency and yield of each method depend on various factors, such as the purity of the starting materials, the reaction conditions, and the expertise of the chemist. Solid-phase peptide synthesis is the most commonly used method for synthesizing (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid, as it allows for the synthesis of large quantities of the compound with high purity and yield.
Environmental and safety considerations should also be taken into account when synthesizing (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid. The use of hazardous chemicals, such as coupling reagents and solvents, should be minimized, and proper waste disposal procedures should be followed to prevent environmental contamination.
Chemical Structure and Biological Activity
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid is a cyclic amino acid derivative that contains a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino group and a carboxylic acid group on the cyclohexene ring. The Fmoc group can be removed using a base, such as piperidine, to expose the amino group for further chemical modification.
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid has been shown to exhibit biological activity, particularly as a building block for the synthesis of peptides and peptidomimetics. It can be incorporated into peptides to enhance their stability and bioactivity, as well as to modulate their conformation and binding affinity to biological targets.
Biological Effects
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid has been shown to have various effects on cell function and signal transduction. It can modulate the activity of enzymes, receptors, and ion channels, as well as affect the expression of genes and proteins involved in cell proliferation, differentiation, and apoptosis.
(1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid has also been investigated for its potential therapeutic and toxic effects. It has been shown to have antimicrobial, antiviral, and anticancer activity, as well as to modulate the immune response and inflammation. However, its toxicity and side effects on human health and the environment need to be further evaluated.
Future Perspectives and Challenges
Despite its potential applications, (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid still faces several challenges and limitations in its use and study. These include the need for further optimization of the synthesis and purification methods, as well as the need for more comprehensive studies on its toxicity and environmental impact.
Possible solutions and improvements include the development of new synthetic methods and purification techniques, as well as the use of alternative protecting groups and coupling reagents that are more environmentally friendly. Future trends and prospects in the application of (1R,2R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acidiaminocyclohex-2-ene-1-carboxylic acid in scientific research include the development of new peptide-based therapeutics and the use of peptides as drug delivery systems and diagnostic tools.

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