16053-39-7Relevant articles and documents
Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics
Biron, Eric,Chatterjee, Jayanta,Kessler, Horst
, p. 2417 - 2420 (2006)
We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole-containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
γ-Valerolactone (GVL): An eco-friendly anchoring solvent for solid-phase peptide synthesis
Al Musaimi, Othman,El-Faham, Ayman,Basso, Alessandra,de la Torre, Beatriz G.,Albericio, Fernando
, (2019/08/26)
Due to the hazardous nature of CH2Cl2, regulatory authorities have imposed restrictions to minimize or even stop its use. It has therefore become imperative to identify environmentally benign solvents to replace it. Here we report on a bio derived solvent, γ-valerolactone, for the incorporation of the first amino acid onto p-alkoxybenzyl alcohol resin in solid-phase peptide synthesis. Satisfactory loading values (by a spectrophotometric method) were achieved. Furthermore, racemization and dipeptide formation were also checked and found to be acceptable.
Biosynthesis of Hyalodendrin and Didethiobis(methylthio)hyalodendrin, Sulphur-containing 2,5-Dioxopiperazines of the 3S,6S Series
Boente, Maria I. Pita,Kirby, Gordon W.,Patrick, Graham L.,Robins, David J.
, p. 1283 - 1290 (2007/10/02)
cyclo-(L-Phe-L-Ser) 8, a known biosynthetic precursor of the (3R,6R)-epidithiodioxopiperazine gliotoxin 4, was efficiently incorporated (42percent), in Hyalodendron sp. (FSC-601) cultures, into the 3S,6S metabolite didethiobis(methylthio)hyalodendrin (DBH) 7 without significant change in the 3H:14C ratio.None of the three diasteromers of cyclo-(L-Phe-L-Ser) was incorporated into DBH to any significant extent.The 13C label from cyclo-(L-Phe-L-Ser) was located, in the expected site, in DBH by 13C NMR spectroscopy.Gliotoxin derived in Gliocladium virens from the doubly labelled precursor 8 was degraded to locate, in similar manner, the 14C label.The N-methyl derivative 16 of cyclo-(L-Phe-L-Ser) was not incorporated detectably into either gliotoxin or DBH.Radioactivity from the doubly labelled, linear dipeptides 17 and 18, possible precursors for the cyclodipeptide 8, was incorporated with moderate efficiency into gliotoxin.However, the 3H:14C ratios for the dipeptides and the derived gliotoxin differd substantially, indicating that the peptides had undergone cleavage in the fungus before incorporation.