79876-22-5Relevant academic research and scientific papers
Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
Lanzi, Matteo,Merad, Jérémy,Boyarskaya, Dina V.,Maestri, Giovanni,Allain, Clémence,Masson, Géraldine
, p. 5247 - 5250 (2018/09/13)
The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.
Synthesis and comparative properties of two amide-generating resin linkers for use in solid phase peptide synthesis
Deng, Fang-Kun,Mandal, Kalyaneswar,Luisier, Sam,Kent, Stephen B.H.
scheme or table, p. 545 - 550 (2011/11/14)
Well-characterized resins of high purity are critical for effective solid phase peptide synthesis (SPPS). The quality of commercial (4-methyl)benzhydrylamine-resin (MBHA-resin), used for the synthesis of peptide amides, is not consistent and residual ketone functionalities are frequently present. Such ketone or aldehyde impurities lead to the formation of acylation-resistant deletion peptides in SPPS. To avoid these undesirable side reactions, we have optimized the preparation of two amide-generating linkers, which, in combination with aminomethyl-resin prepared directly from polystyrene resin, serve as alternatives to MBHA-resin for peptide amide synthesis. Then we have explored their comparative properties in SPPS. Use of sonication in reductive amination facilitated the synthesis of both benzhydrylamine (BHA) and MBHA linkers. We have optimized the preparation of two amide-generating linkers for use in stepwise solid phase peptide synthesis. In combination with aminomethyl-resin prepared directly from polystyrene resin, these linkers serve as alternatives to MBHA-resin for peptide amide synthesis. Copyright
A Gradative Deprotection Strategy for the Solid-Phase Synthesis of Peptide Amides Using p-(Acyloxy)benzhydrylamine Resin and the SN2 Deprotection Method
Tam, James P.
, p. 5291 - 5298 (2007/10/02)
An efficient deprotection strategy for the preparation of peptide amides by solid-phase peptide synthesis is described.The new method, gradative deprotection approach, utilized a multidetachable benzhydrylamine resin, p-(acyloxy)benzhydrylamine resin, and
DESIGN AND SYNTHESIS OF A MULTI-DETACHABLE BENZHYDRYLAMINE-RESIN FOR SOLID PHASE PEPTIDE SYNTHESIS
Tam, James P.,DiMarchi, Richard D.,Merrifield, R. B.
, p. 2851 - 2854 (2007/10/02)
Peptides with C-terminal α-carboxamides were synthesized from a multi-detachable benzhydrylamine-resin containing a Boc-(4-acetoxy)benzhydrylamine handle of unambiguous origin.The peptides bound to the new resin are stable to trifluoroacetic acid, but are cleavable by hydrogen fluoride, base and nucleophiles to give unprotected or protected peptide fragments.
