138775-49-2

Basic information

• Product Name: N-FMoc-3-hydroxy-DL-phenylalanine
• Synonyms: N-FMoc-3-hydroxy-DL-phenylalanine;(9H-Fluoren-9-yl)MethOxy]Carbonyl DL-m-Tyr-OH;N-Fmoc-DL-3-hydroxy-Phenylalanine;Fmoc-DL-m-Tyr-OH
• CAS NO: 138775-49-2
• Molecular Formula: C24H21NO5
• Molecular Weight: 403.42724
• Mol File: 138775-49-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-FMoc-3-hydroxy-DL-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-FMoc-3-hydroxy-DL-phenylalanine(138775-49-2)
• EPA Substance Registry System: N-FMoc-3-hydroxy-DL-phenylalanine(138775-49-2)

Safety Data

• Hazardous Substances Data: 138775-49-2(Hazardous Substances Data)

Usage

General Description

N-FMoc-3-hydroxy-DL-phenylalanine is a chemical compound used in organic synthesis and pharmaceutical research. It is a derivative of phenylalanine, an essential amino acid and a precursor to a number of important neurotransmitters. The N-FMoc-3-hydroxy-DL-phenylalanine compound contains a hydroxyl group at the 3-position of the phenylalanine side chain, and it is often used in the synthesis of peptides and peptidomimetics. Its FMoc (Fluorenylmethyloxycarbonyl) protective group allows for selective deprotection and facilitates the incorporation of the compound into peptide chains. N-FMoc-3-hydroxy-DL-phenylalanine is of interest to researchers in the fields of medicinal chemistry and drug development due to its potential biological and therapeutic properties.

Upstream product

• 775-06-4 D/L-3-hydroxy-phenylalanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 587-33-7 m-tyrosine 

Relevant articles and documents

Optimized Opioid-Neurotensin Multitarget Peptides: From Design to Structure-Activity Relationship Studies

Fusion of nonopioid pharmacophores, such as neurotensin, with opioid ligands represents an attractive approach for pain treatment. Herein, the μ-/δ-opioid agonist tetrapeptide H-Dmt-d-Arg-Aba-β-Ala-NH2(KGOP01) was fused to NT(8-13) analogues. Since the NTS1 receptor has been linked to adverse effects, selective MOR-NTS2 ligands are preferred. Modifications were introduced within the native NT sequence, particularly a β3-homo amino acid in position 8 and Tyr11substitutions. Combination of β3hArg and Dmt led to peptide 7, a MOR agonist, showing the highest NTS2 affinity described to date (Ki= 3 pM) and good NTS1 affinity (Ki= 4 nM), providing a >1300-fold NTS2 selectivity. The (6-OH)Tic-containing analogue 9 also exhibited high NTS2 affinity (Ki= 1.7 nM), with low NTS1 affinity (Ki= 4.7 μM), resulting in an excellent NTS2 selectivity (>2700). In mice, hybrid 7 produced significant and prolonged antinociception (up to 8 h), as compared to the KGOP01 opioid parent compound.