17012-42-9Relevant articles and documents
Two novel cyclic peptides with antifungal activity from the cyanobacterium Tolypothrix byssoidea (EAWAG 195)
Jaki,Zerbe,Heilmann,Sticher
, p. 154 - 158 (2001)
Two novel cyclic tridecapeptides, tolybyssidins A (1) and B (2), were isolated from the culture medium of mass cultured cyanobacterium Tolypothrix byssoidea (EAWAG 195) by means of bioguided isolation. The gross structures of these peptides were determined by 1D and 2D NMR experiments and tandem mass spectrometry. Both peptides contain the nonnatural amino acid dehydrohomoalanine (Dhha) as well as proteinogenic amino acids albeit with D- or L-configuration. The compounds exhibit moderate antifungal activity against the yeast Candida albicans.
Synthesis, stereochemical assignment, and bioactivity of the Penicillium metabolites penicillenols B1 and B2
Kempf, Karl,Schmitt, Florian,Bilitewski, Ursula,Schobert, Rainer
, p. 5064 - 5068 (2015/06/25)
The Penicillium metabolites penicillenols B1 and B2 were synthesised for the first time by elimination of a mesylated penicillenol A precursor as obtained from an l-threonine derived tetramic acid. The (Z,S)- and (E,S)-configured diastereomers were identical to the natural compounds as to NMR spectra and optical rotations. Both isomers showed antiproliferative effects against cancer and endothelial cell lines and penicillenol B1 was also notably antibiotic against Staphylococcus aureus.
A mild removal of Fmoc group using sodium azide
Chen, Chun-Chi,Rajagopal, Basker,Liu, Xuan Yu,Chen, Kuan Lin,Tyan, Yu-Chang,Lin, Fui,Lin, Po-Chiao
, p. 367 - 374 (2014/03/21)
A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected Nα-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs
Duca, Maria,Maloney, David J.,Lodder, Michiel,Wang, Bixun,Hecht, Sidney M.
, p. 4629 - 4642 (2008/03/13)
Described herein is the preparation of new bisacylated tRNAs and their participation in protein synthesis. It has been reported that Thermus thermophilus phenylalanyl-tRNA synthetase can introduce two phenylalanine moieties onto the 3′-terminal adenosine of its cognate tRNA. It is also possible to prepare bisactivated tRNAs in vitro; these participate in protein synthesis [Wang, B.; Zhou, J.; Lodder, M.; Anderson, R. D.; Hecht, S. M. J. Biol. Chem. 2006, 281, 13865]. Presently, the chemical strategy used for the synthesis of the key intermediate bisacylated pdCpAs is described. Bis-S-alanyl- and bis-S-methionyl-pdCpAs were prepared initially. Further, S-threonine, S-allo-threonine, S-homoserine, and (S)-(+)-2-amino-3-hydroxy-3-methylbutyric acid were coupled with the dinucleotide to define preparative methods applicable to more complex amino acids bearing additional functionality in the form of an OH group.
