125882-62-4Relevant articles and documents
Total synthesis of fellutamide b and deoxy-fellutamides B, C, and D
Giltrap, Andrew M.,Cergol, Katie M.,Pang, Angel,Britton, Warwick J.,Payne, Richard J.
, p. 2382 - 2397 (2013)
The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.
Neurotrophic peptide aldehydes: Solid phase synthesis of fellutamide B and a simplified analog
Schneekloth Jr., John S.,Sanders, John L.,Hines, John,Crews, Craig M.
, p. 3855 - 3858 (2006)
A combination of solid phase and solution phase synthetic methods have been used to complete the total synthesis of the neurotrophic lipopeptide aldehyde fellutamide B (2). The β-hydroxy aliphatic tail was prepared by regioselective reductive opening of a cyclic sulfate, and later coupled to a solid phase resin. The synthetic compound was then examined in cytotoxicity and nerve growth factor (NGF) induction assays. A simplified analog of fellutamide B also showed activity.
Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation
Pirrung, Michael C.,Zhang, Fa,Ambadi, Sudhakar,Gangadhara Rao
, p. 8367 - 8375 (2016/09/09)
Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.
Solution phase synthetic approach to fellutamide B
Yadav, Jhillu Singh,Dachavaram, Soma Shekar,Grée, René,Das, Saibal
, p. 3999 - 4001 (2015/06/08)
Abstract A convenient solution phase approach for the synthesis of fellutamide B with efficient purification techniques has been demonstrated on the molecule for the first time. The strategy involves the use of natural amino acids as starting materials and classical peptide coupling reactions. The synthesis has been achieved in 10 steps with overall yield of 26.7% making the synthesis facile.
