64896-33-9Relevant articles and documents
Concise Modular Synthesis of Thalassotalic Acids A-C
Schulz, Joseph M.,Lanovoi, Hunter T.,Ames, Amanda M.,McKegg, Phillip C.,Patrone, James D.
, p. 1045 - 1048 (2019/05/14)
The novel N-acyldehydrotyrosine analogues known as thalassotalic acids A-C were isolated from a marine bacterium by Deering et al. in 2016. These molecules were shown to have tyrosinase inhibition activity and thus are an attractive set of molecules for further study and optimization. To this end, a concise and modular synthesis has been devised and executed to produce thalassotalic acids A-C and two unnatural analogues. This synthesis has confirmed the identity and inhibitory data of thalassotalic acids A-C, more potent synthetic analogues (IC50 = 65 μM), and provides a route for further structure-activity relationship studies to optimize these molecules.
Synthesis of L-threo- and L-erythro-amino acids: novel probes for conformational analysis of peptide side chains
Oba, Makoto,Ueno, Ryuichi,Fukuoka, Mika,Kainosho, Masatsune,Nishiyama, Kozaburo
, p. 1603 - 1610 (2007/10/02)
An efficient and convenient route for the preparation of L-threo- and L-erythro-amino acids 5 as probes for the conformational analysis of peptide side chains by NMR spectroscopy is described.Stereoselective incorporation of deuterium into the α,β-positions of amino acid 5 was accomplished by catalytic deuteration of dehydroamino acid derivatives 1 and 2 followed by a combination of enzymic optical resilution and the racemization at the 2-position.Using these doubly labelled amino acids, it was possible to obtain vicinal coupling constants between carbonyl carbon and prochiral β-protons, J(13C-1Hβ1) and J(13C1-1Hβ2), through 13C NMR spectroscopy alone.We also demonstrate the determination of the fractional populations of rotamers in respect of the Cα-Cβ bond of the amino acids using the measured coupling constants.
