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

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

Uses

Used in Pharmaceutical and Biochemical Research:
N-FMoc-3-hydroxy-L-phenylalanine serves as a key building block in the synthesis of bioactive peptides and proteins. It is used as a precursor for the development of compounds with specific biological activities, enhancing the stability and functionality of the resulting peptides.
Used in Solid-Phase Peptide Synthesis:
In the field of peptide synthesis, N-FMoc-3-hydroxy-L-phenylalanine is utilized as a protected amino acid for the stepwise assembly of peptides. Its FMoc protecting group allows for selective deprotection and coupling reactions, facilitating the production of modified peptides with precise structural requirements.
Used in the Creation of Bioactive Compounds:
N-FMoc-3-hydroxy-L-phenylalanine is employed as a component in the design of bioactive molecules, potentially leading to new pharmaceuticals. Its incorporation can modulate the biological activity of peptides, making it a valuable asset in drug discovery and development.
Used in Biomedical Applications:
N-FMoc-3-hydroxy-L-phenylalanine finds application in the realm of biomaterials, where it contributes to the development of materials with specific biological interactions. Its use in this industry is as a constituent of materials that can be tailored for various medical applications, such as drug delivery systems or tissue engineering scaffolds, due to its ability to influence the properties of the final product.

Upstream product

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

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 
• 872607-66-4 1-benzyloxymethyl-8-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-(9H-fluoren-9-ylmethyl) ester 3-methyl ester 
• 872607-48-2 1-benzyloxymethyl-3-formyl-8-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 872607-64-2 (1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester 

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.

Synthesis of (-)-quinocarcin by directed condensation of α-amino aldehydes

An enantioselective synthesis of the natural antiproliferative agent quinocarcin was achieved by the directed condensation of optically active α-amino aldehyde intermediates. Condensation of the N-protected α-amino aldehyde 1, prepared in eight steps (19% yield) from (R,R)-pseudoephedrine glycinamide, with the C-protected α-amino aldehyde derivative 2, prepared in seven steps (34% yield) from (R,R)-pseudoephedrine glycinamide, afforded the corresponding imine in quantitative yield. Without isolation, direct treatment of this imine intermediate with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and hydrogen cyanide led to cleavage of the fluorenylmethoxycarbonyl (Fmoc) protective group followed by addition of cyanide (Strecker reaction) to form the bis-amino nitriles 3 as a mixture of diastereomers, in 91% yield. Treatment of the diastereomers 3 with trimethylsilyl cyanide and zinc chloride in 2,2,2-trifluoroethanol at 60 °C led to stepwise cyclization to form the tetracyclic product 4 (42% yield from 1 and 2). The latter intermediate was transformed into (-)-quinocarcin (1) in five steps (45% yield). The yield of quinocarcin was 19% from 1 and 2 (7 steps), and 4% from pseudoephedrine glycinamide (15 steps). Copyright