1362858-91-0

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino)-3-phenyl-propionic acid is used as a potential analgesic and anti-inflammatory agent for the treatment of various inflammatory conditions and pain management. Studies have shown its effectiveness in reducing pain and inflammation, although its specific mechanism of action and potential therapeutic applications are still under investigation.

Upstream product

• 84000-03-3 9H-fluoren-9-ylmethyl (S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate 
• 35661-40-6 N-Fmoc L-Phe 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 63-91-2 L-phenylalanine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 1208119-54-3 N-methyl-N-nosyl-L-phenylalanine phenacyl ester 
• 66866-67-9 N-methyl-L-phenylalanine hydrochloride 
• 852852-85-8 N-nosyl-D-phenylalanine 
• 186581-53-3 diazomethane 
• 56564-52-4 N-methyl-D-phenylalanine 
• 18942-49-9 Boc-D-Phe-OH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 106327-80-4 H-Tyr-D-Orn[*]-Phe(NMe)-Asp[*]-NH₂ 
• 868840-74-8 C₄₉H₇₄N₈O₁₃S 
• 873951-99-6 Me₂Leu-Ser(Me₂Leu-Ser-MeLeu-MePhe)-MeLeu-MePhe-OH 
• 873951-96-3 Me₂Leu-Ser-MeLeu-MePhe-OH 

Relevant academic research and scientific papers

Facile synthesis of Fmoc-N-methylated α- and β-amino acids

A highly efficient and environmentally friendly synthesis of Fmoc-N-methyl α- and β-amino acids from the corresponding Fmoc-amino acid, via intermediate oxazolidinones/oxazinanones, has been developed. Microwave heating for 3 min was required for the synt

A new GLP-1 analogue with prolonged glucose-lowering activity in vivo via backbone-based modification at the N-terminus

Glucagon-like peptide-1 (GLP-1) is an endogenous insulinotropic hormone with wonderful glucose-lowering activity. However, its clinical use in type II diabetes is limited due to its rapid degradation at the N-terminus by dipeptidyl peptidase IV (DPP-IV). Among the N-terminal modifications of GLP-1, backbone-based modification was rarely reported. Herein, we employed two backbone-based strategies to modify the N-terminus of tGLP-1. Firstly, the amide N-methylated analogues 2-6 were designed and synthesized to make a full screening of the N-terminal amide bonds, and the loss of GLP-1 receptor (GLP-1R) activation indicated the importance of amide H-bonds. Secondly, with retaining the N-terminal amide H-bonds, the β-peptide replacement strategy was used and analogues 7-13 were synthesized. By two rounds of screening, analogue 10 was identified. Analogue 10 greatly improved the DPP-IV resistance with maintaining good GLP-1R activation in vitro, and showed approximately a 4-fold prolonged blood glucose-lowering activity in vivo in comparison with tGLP-1. This modification strategy will benefit the development of GLP-1-based anti-diabetic drugs.

Improving oral bioavailability of peptides by multiple N-methylation: Somatostatin analogues

Full methyl jacket? A complete library of the N-methylated somatostatin cyclopeptidic analogue Veber-Hirschmann peptide cyclo(-PFwKTF-) has been prepared with the aim of improving its bioavailability. Several analogues from the library were found to bind

First total synthesis of hoshinoamide A

Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hosh

Isostearyl Mixed Anhydrides for the Preparation of N-Methylated Peptides Using C-Terminally Unprotected N-Methylamino Acids

Sustainable and efficient manufacturing methods for N-methylated peptides remain underexplored despite growing interest in therapeutic N-methylated peptides within the pharmaceutical industry. A methodology for the coupling of C-terminally unprotected N-methylamino acids mediated by an isostearic acid halide (ISTAX) and silylating reagent has been developed. This approach allows for the coupling of a wide variety of amino acids and peptides in high yields under mild conditions without the need for a C-terminal deprotection step in the process of C-terminal elongation. These advantages make this a useful synthetic method for the production of peptide therapeutics and diagnostics containing N-methylamino acids.

Iridium-Catalyzed Asymmetric Hydrogenation of N-Alkyl α-Aryl Furan-Containing Imines: an Efficient Route to Unnatural N-Alkyl Arylalanines and Related Derivatives

High throughput experimentation (HTE) has enabled the rapid identification of ligand/precatalyst combinations that facilitate highly enantioselective hydrogenations of prochiral N-alkyl α-aryl ketimines containing a furyl moiety. The chiral amines obtained have proven to be modular precursors in the synthesis of unnatural mono N-alkylated arylalanines and related derivatives. (Figure presented.).

Investigation for the cyclization efficiency of linear tetrapeptides: Synthesis of tentoxin B and dihydrotentoxin

Investigation of the cyclization efficiency of N-methyl linear tetrapeptides using a molecular modeling study and chemical synthesis is described. The linear peptide with two N-methyl groups, MeAla-Leu-MePhe-Gly, forms γ-turn like conformation with the am

A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods

[2S,3S-Hmp]-Aureobasidin L 2 has been successfully synthesised through a combination of solution- and solid-phase peptide synthesis. All of the Fmoc-protected residues including a depsidipeptide, Fmoc-MeVal-Hmp-OH, were prepared in solution phase. Chain e

Fluorenylmethoxycarbonyl-N-methylamino acids synthesized in a flow tube-in-tube reactor with a liquid-liquid semipermeable membrane

Both steps of the N-methylation of 9-fluorenylmethoxycarbonyl (Fmoc) amino acids were carried out in a microstructured tube-in-tube reactor equipped with a semipermeable Teflon AF 2400 membrane as the inner tubing. In the first step, gaseous formaldehyde

Enantioselective total synthesis of eudistomidins G, H, and I

Asymmetric first total synthesis of eudistomidins G, H, and I, tetrahydro-β-carboline alkaloids from the Okinawan marine tunicate Eudistoma glaucus, has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configurations of eudistomidins G, H, and I were confirmed from comparison of the 1H and 13C NMR, and CD spectral data of synthetic and natural eudistomidins G, H, and I, respectively.