98385-71-8Relevant academic research and scientific papers
Visible-Light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes
Reimler, Jannik,Studer, Armido
supporting information, p. 15392 - 15395 (2021/10/04)
A method for the selective tryptophan modification and labelling of tryptophan-containing peptides is described. Photoirradiation of acylsilanes generates reactive siloxycarbenes which undergo H?N-insertion into the indole moiety of tryptophan to give stable silyl protected hemiaminals. This method is successfully applied to chemically modify various tryptophan containing oligopeptides. The method enables the selective introduction of alkynes to peptides that are eligible for further alkyne-azide click chemistry. In addition, the dansyl fluorophore can be conjugated to a peptide using this approach.
Cu-Catalyzed Site-Selective C(sp2)-H Radical Trifluoromethylation of Tryptophan-Containing Peptides
Correa, Arkaitz,Guerrero, Itziar
supporting information, p. 1754 - 1759 (2020/03/23)
Site-selective functionalization of C-H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp2)-H trifluoromethylation of tryptophan (Trp)-containing peptides. This fluorination technique is characterized by its chirality preservation, tolerance of functional groups, and scalability and exhibits chemoselectivity for Trp residues over other amino acid and heterocyclic units. As a result, it represents a sustainable tool toward the late-stage peptide modification and protein engineering.
Synthesis and characterization of peptide-cationic steroid antibiotic conjugates
Ding, Bangwei,Taotofa, Uale,Orsak, Thomas,Chadwell, Matthew,Savage, Paul B.
, p. 3433 - 3436 (2007/10/03)
(Chemical Equation Presented) New cationic steroid antibiotics have been prepared by conjugating tripeptides to a triamino analogue of cholic acid. These compounds were synthesized on a solid phase in an indexed library that was screened for antibacterial
