178432-48-9

Basic information

• Product Name: N-FMoc-3-hydroxy-L-phenylalanine
• Synonyms: N-FMoc-3-hydroxy-L-phenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid;(9H-Fluoren-9-yl)MethOxy]Carbonyl L-m-Tyr-OH;N-Fmoc-L-3-hydroxy-Phenylalanine
• CAS NO: 178432-48-9
• Molecular Formula: C₂₄H₂₁NO₅
• Molecular Weight: 403.42724
• Mol File: 178432-48-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 673.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.336±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.79±0.10(Predicted)
• CAS DataBase Reference: N-FMoc-3-hydroxy-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-FMoc-3-hydroxy-L-phenylalanine(178432-48-9)
• EPA Substance Registry System: N-FMoc-3-hydroxy-L-phenylalanine(178432-48-9)

Safety Data

• Hazardous Substances Data: 178432-48-9(Hazardous Substances Data)

Usage

General Description

N-FMoc-3-hydroxy-L-phenylalanine is a chemical compound used in the synthesis of peptides and proteins. It is a derivative of the amino acid phenylalanine, which contains a hydroxy group at the 3-position and is protected with a FMoc (9-fluorenylmethoxycarbonyl) group. N-FMoc-3-hydroxy-L-phenylalanine is commonly utilized in solid-phase peptide synthesis for the production of modified peptides with specific structural and functional properties. N-FMoc-3-hydroxy-L-phenylalanine may also be employed as a building block for the creation of bioactive compounds, pharmaceuticals, and materials with biomedical applications, due to its potential to modulate the biological activity and stability of peptides. Overall, N-FMoc-3-hydroxy-L-phenylalanine plays an important role in the development of molecular tools for biological and medicinal research.

Upstream product

• 587-33-7 m-tyrosine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 178432-33-2 (S)-3-[3-(Diethoxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 
• 236393-09-2 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-hydroxy-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 
• 167935-97-9 methyl (S)-2-amino-3-(3-hydroxyphenyl)propanoate 
• 872607-49-3 (E)-(2S,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile 
• 872607-53-9 (Z)-(2S,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile 
• 872607-52-8 (E)-(2R,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile 
• 872607-54-0 (Z)-(2R,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile 

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.