72155-48-7

Basic information

• Product Name: BOC-AHPPA
• Synonyms: N-GAMMA-T-BUTOXYCARBONYL-(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID;N-T-BOC-(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID;N-ALPHA-T-BOC-(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID;BOC-(S,S)AHPPA-OH;BOC-PHENYLSTATINE;BOC-PHE-STATINE;BOC-AHPPA;BOC-AHPPA-OH
• CAS NO: 72155-48-7
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.36
• Mol File: 72155-48-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 88 °C
• Boiling Point: 528.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.191±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.21±0.10(Predicted)
• CAS DataBase Reference: BOC-AHPPA(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-AHPPA(72155-48-7)
• EPA Substance Registry System: BOC-AHPPA(72155-48-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 72155-48-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 100-52-7 benzaldehyde 
• 237057-09-9 Boc-4-amino-3-hydroxy-5-phenylpentanoic acid ethyl ester 
• 101669-80-1 methyl (3S,4S)-N-tert-butoxycarbonyl-4-amino-3-hydroxy-5-phenylpentanoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 885859-80-3 (3S,4S)-4-Amino-5-phenyl-pentane-1,3-diol 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 114671-12-4 (4S,5S)-5-ethenyl-4-phenylmethyloxazolidin-2-one 
• 114671-09-9 N-(tert-butyldimethylsilyloxycarbonyl)-4-amino-1-chloro-5-phenyl-2-pentene 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 124818-81-1 (4S)-N-(tert-botoxycarbonyl)-4-amino-1-chloro-5-phenyl-2-pentene 
• 124818-93-5 (4S)-4-(N-tert-butoxycarbonyl)amino-5-phenyl-2-penten-1-ol 
• 112700-36-4 (2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 112700-41-1 (5S)-5-benzyl-1-(tert-butyloxycarbonyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one 
• 4530-18-1 N-(tert-butoxycarbonyl)-L-phenylalanine 

Downstream Products

• 215511-54-9 (S)-2-[(2S,3S)-2-((3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenyl-pentanoylamino)-3-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 
• 72155-66-9 N-(tert-butoxycarbonyl)-4(S)-amino-3(S)-hydroxy-5-phenylpentanoyl-L-alanyl isoamylamide 
• 98105-45-4 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid 
• 72155-50-1 (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid 
• 172912-04-8 BocAHPPA-Phe-Leu-Phe 

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.

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.

Stereoselective synthesis of (-)-N-Boc-AHPPA

An efficient method has been developed for the stereoselective synthesis of N-Boc-AHPPA (7), a biologically important amino acid of non-proteinogenic origin.