- New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis
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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.
- Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa
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p. 3709 - 3718
(2008/02/10)
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- Glucagon antagonists/inverse agonists
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A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism, such as dyslipidemia, and obesity.
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- New Efficient Strategy for the Incorporation of (S)-Isoserine into Peptides
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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.
- Burger, Klaus,Windeisen, Elisabeth,Pires, Raul
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p. 7641 - 7645
(2007/10/03)
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