161125-36-6Relevant articles and documents
New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis
Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa
, p. 3709 - 3718 (2008/02/10)
A synthesis of a series of N-alkoxycarbonyl mercaptobenzothiazoles (MBTs) and their application as reagents for chemoselective protection of amino group are presented herein. It was shown that all new reagents, Z-MBT, Fmoc-MBT, Phoc-MBT, and Tec-MBT, are highly effective in the selective N-alkoxycarbonylation of (S)-isoserine. The transformation is a simple, fast, and low-cost protocol, which is applicable in scale-up experiments. The starting MBT was fully recovered at the end of the process, which is an additional advantage of the method. The efficiency of the Z-reagent was also demonstrated by the selective protection of both gentamicin B and (S)-isoserine before their peptide-type coupling in the synthesis of the aminoglycoside antibiotic isepamicin. Copyright Taylor & Francis Group, LLC.
New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides
Burger, Klaus,Windeisen, Elisabeth,Pires, Raul
, p. 7641 - 7645 (2007/10/03)
A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described.Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.
