213667-61-9Relevant academic research and scientific papers
Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment
Hutton, Craig A.,Shabani, Sadegh,White, Jonathan M.
supporting information, p. 7730 - 7734 (2020/10/09)
The total synthesis of the putative structure of asperipin-2a is described. The synthesis features ether cross-links between the phenolic oxygen of Tyr6 and the β position of Tyr3 and the phenolic oxygen of Tyr3 and the β position of Hpp1 in the unique 17- and 14-membered bicyclic structure of asperipin-2a, respectively. The synthesized putative structure does not match the natural product, and a stereochemical reassignment is postulated.
Synthesis of the C-Terminal Macrocycle of Asperipin-2a
Shabani, Sadegh,White, Jonathan M.,Hutton, Craig A.
supporting information, (2019/03/19)
A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the β-position of Tyr3. Comparison of NMR data of the natural product with these isomers and X-ray
Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry
Crich, David,Sana, Kasinath
supporting information; experimental part, p. 7383 - 7388 (2010/01/16)
(Chemical Equation Presented) A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H- fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods. 2009 American Chemical Society.
Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides
Alsina, Jordi,Rabanal, Francesc,Chiva, Cristina,Giralt, Ernest,Albericio, Fernando
, p. 10125 - 10152 (2007/10/03)
N,N'-disuccinimidyl carbonate (DSC) has been successfully used to generate carbonates and carbamates on conventional hydroxymethyl and aminomethyl based resins. This methodology extends the applicability of such linkers, which were initially designed for
Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides
Alsina, Jordi,Chiva, Cristina,Ortiz, Marta,Rabanal, Francesc,Giralt, Ernest,Albericio, Fernando
, p. 883 - 886 (2007/10/03)
N,N'-Disuccinimidyl carbonate (DSC) has been successfully used for the efficient conversion of 4-hydroxymethylpolystyrene and 4-hydroxymethyl-3-nitrobenzamido (Nbb) resins into active carbonate resins, which are suitable for the incorporation of molecules
