75530-96-0Relevant academic research and scientific papers
Solid-phase combinatorial synthesis of peptide-biphenyl hybrids as calpain inhibitors
Montero, Ana,Albericio, Fernando,Royo, Miriam,Herradon, Bernardo
, p. 4089 - 4092 (2004)
(Chemical Equation Presented) The combinatorial parallel synthesis of peptide-biphenyl hybrids on solid support using state of the art of peptide synthesis is reported. Key steps were the N to C addition of an amino moiety, hydrolysis of the methyl ester,
ANTIBACTERIAL COMPOUNDS
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Page/Page column 39; 41, (2014/10/15)
The invention relates to antibacterial compounds, methods for synthesis and use thereof in antibacterial applications.
Versatile method for the detection of covalently bound substrates on solid supports by DART mass spectrometry
Sanchez, Laura M.,Curtis, Matthew E.,Bracamonte, Bianca E.,Kurita, Kenji L.,Navarro, Gabriel,Sparkman, O. David,Linington, Roger G.
supporting information; experimental part, p. 3770 - 3773 (2011/10/02)
Analysis of substrates directly on solid phase resins without the need for separate cleavage conditions remains an outstanding challenge in the field of solid phase synthesis. We now present the first example of simultaneous cleavage and mass spectrometri
Peptide cyclization and cyclodimerization by CuI-mediated azide-alkyne cycloaddition
Jagasia, Reshma,Holub, Justin M.,Bollinger, Markus,Kirshenbaum, Kent,Finn
experimental part, p. 2964 - 2974 (2009/09/26)
Head-to-tail cyclodimerization of resin-bound oligopeptides bearing azide and alkyne groups occurs readily by 1,3-dipolar cycloaddition upon treatment with CuI. The process was found to be independent of peptide sequence, sensitive to the proximity of the alkyne to the resin, sensitive to solvent composition, facile for a- and β-peptides but not for γ-peptides, and inhibited by the inclusion of tertiary amide linkages. Peptides shorter than hexamers were predominantly converted to cyclic monomers. Oligoglycine and oligo(β-alanine) chains underwent oligomerization by 1,3-dipolar cycloaddition in the absence of a copper catalyst. These results suggest that cyclodimerization depends on the ability of the azido-alkyne peptide to form in-frame hydrogen bonds between chains in order to place the reacting groups in close proximity and lower the entropic penalty for dimerization. The properties of the resin and solvent are crucial, giving rise to a productive balance between swelling and interstrand H-bonding. These findings allow for the design of optimal substrates for triazole-forming ring closure and for the course of the reaction to be controlled by the choice of conditions.
