162536-46-1

Basic information

• Product Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-(phenylmethoxy)-
• CAS NO: 162536-46-1
• Molecular Formula: C21H25NO5
• Molecular Weight: 371.433
• Mol File: 162536-46-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-(phenylmethoxy)-(162536-46-1)
• EPA Substance Registry System: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-(phenylmethoxy)-(162536-46-1)

Safety Data

• Hazardous Substances Data: 162536-46-1(Hazardous Substances Data)

Upstream product

• 162536-45-0 benzyl (S)-3-(3-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 587-33-7 m-tyrosine 
• 90819-30-0 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 1026869-14-6 [(S)-1-(3-Benzyloxy-benzyl)-3-chloro-2-oxo-propyl]-carbamic acid tert-butyl ester 
• 162538-24-1 [(S)-3-((S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butylamino)-2-hydroxy-1-(3-hydroxy-benzyl)-propyl]-carbamic acid tert-butyl ester 
• 162538-23-0 [(S)-1-(3-Benzyloxy-benzyl)-3-((S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Constraining the Side Chain of C-Terminal Amino Acids in Apelin-13 Greatly Increases Affinity, Modulates Signaling, and Improves the Pharmacokinetic Profile

Side-chain-constrained amino acids are useful tools to modulate the biological properties of peptides. In this study, we applied side-chain constraints to apelin-13 (Ape13) by substituting the Pro12 and Phe13 positions, affecting the binding affinity and signaling profile on the apelin receptor (APJ). The residues 1Nal, Trp, and Aia were found to be beneficial substitutions for Pro12, and the resulting analogues displayed high affinity for APJ (Ki 0.08-0.18 nM vs Ape13 Ki 0.7 nM). Besides, constrained (d-Tic) or α,α-disubstituted residues (Dbzg; d-α-Me-Tyr(OBn)) were favorable for the Phe13 position. Compounds 47 (Pro12-Phe13 replaced by Aia-Phe, Ki 0.08 nM) and 53 (Pro12-Phe13 replaced by 1Nal-Dbzg, Ki 0.08 nM) are the most potent Ape13 analogues activating the Gα12 pathways (53, EC50 Gα12 2.8 nM vs Ape13, EC50 43 nM) known to date, displaying high affinity, resistance to ACE2 cleavage as well as improved pharmacokinetics in vitro (t1/2 5.8-7.3 h in rat plasma) and in vivo.

Compounds participating in cooperative association and uses thereof

The invention features compounds (e.g., macrocyclic compounds) capable of modulating biological processes, for example through binding to a presenter protein (e.g., a member of the FKBP family, a member of the cyclophilin family, or PIN1) and a target protein (e.g., a eukaryotic target protein such as a mammalian target protein or a fungal target protein or a prokaryotic target protein such as a bacterial target protein). These compounds bind endogenous intracellular presenter proteins, such as the FKBPs or cyclophilins, and the resulting binary complexes selectively bind and modulate the activity of intracellular target proteins. Formation of a tripartite complex among the presenter protein, the compound, and the target protein is driven by both protein-compound and protein-protein interactions, and both are required for modulation of the targeted protein's activity.