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

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

Uses

Used in Pharmaceutical Research:
N-FMoc-3-hydroxy-DL-phenylalanine is used as a building block in the synthesis of peptides and peptidomimetics for the development of new drugs. Its FMoc protective group allows for selective deprotection, facilitating the incorporation of the compound into peptide chains and enhancing the efficiency of drug synthesis.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-FMoc-3-hydroxy-DL-phenylalanine is used as a key intermediate in the design and synthesis of bioactive molecules with potential therapeutic properties. Its unique structure and functional groups enable the development of novel compounds with specific biological activities.
Used in Organic Synthesis:
N-FMoc-3-hydroxy-DL-phenylalanine is employed as a versatile reagent in organic synthesis, allowing for the preparation of a wide range of chemical compounds. Its hydroxyl and amino acid functionalities can be further modified or used in the formation of various chemical bonds, expanding the scope of synthetic applications.
Used in Neurotransmitter Research:
As a derivative of phenylalanine, N-FMoc-3-hydroxy-DL-phenylalanine is utilized in research related to neurotransmitters, which are essential for the proper functioning of the nervous system. Its potential involvement in the synthesis or modulation of neurotransmitter activity makes it a valuable tool for understanding and developing treatments for neurological disorders.

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.

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