153061-61-1

Basic information

• Product Name: (3R,4R)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID
• Synonyms: (3R,4R)-AHPPA-OH;(3R,4R)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID
• CAS NO: 153061-61-1
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.24
• Mol File: 153061-61-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,4R)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID(153061-61-1)
• EPA Substance Registry System: (3R,4R)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID(153061-61-1)

Safety Data

• Hazardous Substances Data: 153061-61-1(Hazardous Substances Data)

Usage

General Description

(3R,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid, also known as L-phenylalanine, is an essential amino acid that is important for protein synthesis and various other biochemical processes in the body. It is found in various food sources such as meat, fish, eggs, and dairy products. L-phenylalanine is also used as a dietary supplement and has been studied for its potential therapeutic effects in conditions such as depression, pain management, and skin disorders. It is a precursor for the neurotransmitters dopamine, norepinephrine, and epinephrine, and is involved in the production of melanin, the pigment responsible for skin and hair color. However, excessive intake of phenylalanine can be harmful for individuals with the genetic disorder phenylketonuria (PKU), as they cannot metabolize this amino acid properly.

Upstream product

• 390377-68-1 (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid 
• 72155-45-4 Boc-L-phenylalaninal 
• 111871-62-6 (Z)-(S)-4-Benzyloxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester 
• 132549-34-9 (S)-((4S,5R)-4-Benzyl-2-oxo-oxazolidin-5-yl)-iodo-acetic acid methyl ester 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 390377-67-0 (3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid 
• 210964-89-9 (+)-(4S,5S)-5-benzyl-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone 
• 132549-37-2 methyl (4S,5S)-4-benzyl-2-oxooxazolidine-5-acetate 
• 72155-48-7 (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid 
• 188774-99-4 tert-butyl 4-(N,N-dibenzylamino)-3-oxo-5-phenylpentanoate 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 
• 63-91-2 L-phenylalanine 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 

Relevant articles and documents

Helices with additional H-bonds: crystallographic conformations of α,γ-hybrid peptides helices composed of β-hydroxy γ-amino acids (statines)

β-Hydroxy-γ-amino acids (Statines) are a class of naturally occurring non-ribosomal amino acids frequently found in many peptide natural products. Peptidomimetics constituted with statines have been used as inhibitors for various aspartic acid proteases. In contrast to the synthetic γ-amino acids, very little is known about the folding behavior of these naturally occurring β-hydroxy γ-amino acids. To understand the folding behavior of statines, three α,γ-hybrid peptides P1 (Ac-Aib-γPhe-Aib-(R, S)Phesta-Aib-γPhe-Aib-CONH2), P2 (Ac-Aib-γPhe-Aib-(S, S)Phesta-Aib-γPhe-Aib-CONH2), and P3 (Ac-Aib-γPhe-Aib-(S, S)Phesta-Aib-(S, S)Phesta-Aib-CONH2) were synthesized on solid phase and their helical conformations in single crystals were studied. Results suggest that both syn and anti diastereoisomers of statines can be accommodated into the helix without deviating overall helical conformation of α,γ-hybrid peptides. In comparison with syn diastereoisomer, the anti diastereoisomer was found to be directly involved in the intramolecular H-bonding with the backbone carbonyl groups (i to i + 3) similar to the backbone amide NHs in the helix.

Application of the asymmetric aminohydroxylation reaction for the syntheses of HIV-protease inhibitor, hydroxyethylene dipeptide isostere and γ-amino acid derivative

An enantioselective synthesis of lactone 1, a precursor to the (2R,4S,5S) hydroxyethylene dipeptide isostere and amino acid AHPPA 2 has been accomplished from the common intermediate 5 employing Sharpless asymmetric aminohydroxylation as the key step.

Solid-Phase Synthesis of β-Lactams via the Miller Hydroxamate Approach

(Matrix Presented) β-Lactams were prepared on solid phase starting from serine, threonine, or other β-hydroxyacids derived from naturally occurring amino acids and a resin bound hydroxylamine. The ring closure was carried out under Mitsunobu conditions. The amino group present on the β-lactam was used to assemble a short peptide. After a reductive cleavage with Sml2, β-lactam-containing peptides were obtained.