59095-84-0

Upstream product

• 27601-29-2 t-butyloxycarbonyl-O-benzyl-L-tyrosine hydroxysuccinimide ester 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 911675-15-5 Z-(7-bromo)Trp-NHMe 
• 73183-34-3 bis(pinacol)diborane 
• 642073-54-9 N-Boc-3-iodo-Tyr(Bzl)-Ala-OMe 

Downstream Products

• 642073-54-9 N-Boc-3-iodo-Tyr(Bzl)-Ala-OMe 
• 65671-30-9 Boc-Tyr(Bzl)-D-Ala-OH 
• 944059-34-1 N-(tert-butoxycarbonyl)-3-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)]-Tyr(Bn)-Ala-OMe 
• 911675-65-5 N-Boc-Tyr(Bn)-Ala-Trp-OCH₃ 
• 911675-44-0 N-Boc-Tyr(Bn)-Ala-Trp-NHCH₂Ph 
• 911675-67-7 N-Boc-Tyr(Bn)-Ala-Trp-OH 
• 700376-95-0 N-Boc-3-iodo-Tyr(Bn)-Ala-OH 
• 642073-57-2 N-Boc-3-iodo-Tyr(Bn)-AIa-7-bromo-Trp-OMe 
• 1628630-17-0 C₁₉H₂₀N₂O₃ 

Relevant academic research and scientific papers

Synthesis and conformational characterization of diketopiperazines bearing a benzyl moiety

Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1HNMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1HNMR spectra. An intramolecular CH-π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.

Linear TMC-95-based proteasome inhibitors

We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and

COMPOUNDS USEFUL AS MODULATORS OF THE PROTEASOME ACTIVITY

The present invention relates to the use of compounds of the following general formula (I): wherein no is 0 or 1, and when no is 1, X = CH2 or X = NCH2C6H5; R1 is OH, or a OR10 group, or a group of formula NH-(CH2)n1-R11; R2 is H, or an alkyl group, or a group of formula (CH2)n2-(CO)n3-NR13R14; R3 is H, or an alkyl group; R4 is H, or Boc, or Z; R5 is H, or Boc, or Z ; R6 is a OR16 group; R7 and R8 are H, or a halogen atom, as modulators of the proteasome activity, in the frame of the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, or the preparation of cosmetic compositions, or of phytosanitary compositions.

Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A

The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.