189062-72-4

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 13122-90-2 Boc-Phe-Phe-OH 
• 3674-06-4 Boc-Phe-ONSu 
• 13122-89-9 (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 54613-88-6 Boc-Phe-Phe-Trp-OH 
• 108456-12-8 Boc-L-Phe-L-Phe-L-Phe-OH 
• 1419186-31-4 C₇₅H₉₆N₁₀O₁₂ 
• 293732-69-1 N¹,N²-bis(L-Phe-L-Phe)ethanediamine 
• 293732-75-9 1,2-ethano-bis(L-Phe-L-PheBoc) 
• 143674-01-5 Boc-Phe-Phe-Trp-NHOH 
• 143674-00-4 Boc-Phe-Phe-Asp(β-NHOH)-OH 
• 143673-99-8 Boc-Phe-Phe-Asp(β-OBzl)-OH 

Relevant academic research and scientific papers

Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates

Abstract: Dipeptide 3, tetrapeptide 4 and pentapeptide 5, containing adamantylphthalimide and tyrosine, were synthesized and their photochemical reactivity investigated. Upon excitation to the triplet excited state, 3 does not give any photoproduct, although the photoinduced electron transfer (PET) should take place based on the thermodynamic properties. Tetrapeptide 4 and pentapeptide 5 are photochemically reactive, undergoing decomposition upon excitation. The lack of anticipated photodecarboxylation reactivity is explained by PET between the tyrosine and the phthalimide. However, deprotonation of the phenoxyl radical-cation giving phenoxyl radicals or back electron transfer giving starting material are probably faster than intrastrand single electron transfer which would lead to carboxyl radical and decarboxylation. The results indicate the importance of fine-tuning the molecular structure to attain the desired photoreactivity by the right choice of the reactants redox potential, as well as their acid/base properties.

Photocyclization of Tetra- and Pentapeptides Containing Adamantylphthalimide and Phenylalanines: Reaction Efficiency and Diastereoselectivity

A series of tetrapeptides and pentapeptides was synthesized bearing a phthalimide chromophore at the N-terminus. The C-terminus of the peptides was strategically substituted with an amino acid, Phe, Phe(OMe), or Phe(OMe)2 characterized by different oxidation potentials. The photochemical reactivity of the peptides was investigated by preparative irradiation and isolation of photoproducts, as well as with laser flash photolysis. Upon photoexcitation, the peptides undergo photoinduced electron transfer (PET) and decarboxylation, followed by diastereoselective cyclization with the retention of configuration for tetrapeptides or inversion of configuration for pentapeptides. Molecular dynamics (MD) simulations and NOE experiments enabled assignment of the stereochemistry of the cyclic peptides. MD simulations of the linear peptides disclosed conformational reasons for the observed diastereoselectivity, being due to the peptide backbone spatial orientation imposed by the Phe amino acids. The photochemical efficiency for the decarboxylation and cyclization is not dependent on the peptide length, but it depends on the oxidation potential of the amino acid at the C-terminus. The results described herein are particularly important for the rational design of efficient photochemical reactions for the preparation of cyclic peptides with the desired selectivity.

Spacer driven morphological twist in Phe-Phe dipeptide conjugates

Chemists and material scientists are interested in complex biological systems and morphologies for fabrication of new materials. Bioinspired design of short peptide conjugates produces various self-assembled structures, depending on their structural diver

Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues

A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized.Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology an