90982-83-5Relevant academic research and scientific papers
C-H Functionalization of N-Methylated Amino Acids and Peptides as Tool in Natural Product Synthesis: Synthesis of Abyssenine A and Mucronine e
Kinsinger, Thorsten,Kazmaier, Uli
supporting information, p. 7726 - 7730 (2018/12/11)
N-Methylated amino acids and peptides with an 8-aminoquinoline (AQ) directing group can be subjected to stereoselective Pd-catalyzed β-functionalizations. The best results are obtained with aryl iodides, but alkyl and alkenyl side chains can also be introduced. The AQ protecting group can easily be removed, providing the free carboxylic acid, which can be used directly in peptide couplings. This protocol was used successfully as a key step in the synthesis of the cyclopeptide alkaloids abyssenine A and mucronine E.
Total synthesis of the cyclopeptide alkaloid abyssenine A. Application of inter- and intramolecular copper-mediated coupling reactions in organic synthesis
Toumi, Mathieu,Couty, Francois,Evano, Gwilherm
, p. 9003 - 9009 (2008/03/13)
(Chemical Equation Presented) The first total synthesis of the 15-membered ring cyclopeptide alkaloid abyssenine A 1 has been achieved with a longest linear sequence of 15 steps. Central to the synthetic approach was an efficient copper-mediated Ullmann c
Synthesis of a Wasp Venom Tetradecapeptide, Mastoparan, with a New Cleaving System for 4-Methoxy-2,2,6-trimethylbenzenesulfonyl (Mtr) Amino-Protecting Group
Saito, Kazuki,Higashijima, Tsutomu,Miyazawa, Tatsuo,Wakimasu, Mitsuhiro,Fujino, Masahiko
, p. 2187 - 2193 (2007/10/02)
The 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr) group was introduced for protection of the ε-amino function of lysine and its acid lability was examined.The cleavage of Lys(Mtr) was accelerated by addition of methyl sulfide, as a second scavenger, to methanesulfonic acid-containing trifluoroacetic acid-thioanisole.In order to examine the usefulness of the new cleaving system with methyl sulfide, a wasp venom peptide, mastoparan, was synthesized.This system was found to give a highly pure product in good yield.Keywords - 4-methoxy-2,3,6-trimethylbenzenesulfonyl (Mtr); Nε-4-methoxy-2,3,6-trimethylbenzenesulfonyllysine; methanesulfonic acid-trifluoracetic acid-thioanisole-methyl sulfide deprotection; mastoparan; wasp venom peptide
