152491-85-5Relevant articles and documents
Synthesis of an (R)-Garner-type aldehyde from L-serine: Useful building block for a (+)-furanomycin derivative
Bartoli, Giuseppe,Di Antonio, Giustino,Fiocchi, Roberto,Giuli, Sandra,Marcantoni, Enrico,Marcolini, Mauro
, p. 951 - 956 (2009)
(+)-Furanomycin is an antibiotic that substitutes for L-isoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid L-serine, and via a Garner-type aldehyde. The (R)-α-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of L-serine. Georg Thieme Verlag Stuttgart.
Application of the highly sensitive labeling reagent to the structural confirmation of readily isomerizable peptides
Pan, Chengqian,Kuranaga, Takefumi,Kakeya, Hideaki
, p. 339 - 343 (2021)
Thioamycolamide A (1) is a biosynthetically unique cytotoxic cyclic microbial lipopeptide that bears a d-configured thiazoline, a thioether bridge, a fatty acid side chain, and a reduced C-terminus. It has gained attention for its unique structure, and very recently we reported the total synthesis of 1 via a biomimetic route. The NMR spectra of synthetic 1 agreed with those of natural 1. However, structural identity between peptidic natural and synthetic compounds is often difficult to confirm by comparison of NMR spectra because their NMR spectra vary depending on the conditions in the NMR tube, which often result in the structural misassignment of peptidic compounds. Especially, our total synthesis based on the putative biomimetic route potentially gives 1 as a diastereomixture at the final step. The problem is that the diastereomers of peptidic mid-sized molecules often exhibit similar properties (such as NMR spectra and bioactivities), and their separation procedures are often laborious. Herein we report the structural confirmation of synthetic 1 by the LC–MS-based chromatographic comparison with the use of our highly sensitive labeling reagent l-FDVDA; the highly sensitive-advanced Marfey’s method (HS-advanced Marfey’s method). This work demonstrated the utility of our highly sensitive labeling reagent for the structural determination of not only scarce natural products but also readily isomerizable synthetic compounds.
CYCLIC COMPOUNDS AND METHODS OF USING SAME
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, (2021/06/11)
The present application relates to compounds of Formula (I), as defined herein, and pharmaceutically acceptable salts thereof. The present application also describes pharmaceutical composition comprising a compound of Formula (I), and pharmaceutically acc
MACROCYCLIC KINASE INHIBITORS AND THEIR USE
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Paragraph 0437; 0440, (2019/07/13)
The present disclosure relates to certain chiral diaryl macrocyclic derivatives, pharmaceutical compositions containing them, and methods of using them to treat cancer, pain, neurological diseases, autoimmune diseases, and inflammation.
