220498-02-2Relevant articles and documents
Backbone modifications in peptidic inhibitors of flaviviral proteases
Jakob, Alexander K.M.H.,Sundermann, Tom R.,Klein, Christian D.
supporting information, p. 1913 - 1917 (2019/06/08)
The NS2B-NS3 protease is a promising target for the development of drugs against dengue virus (DENV), West Nile virus (WNV) and related flaviviruses. We report the systematic variation of the peptide backbone of the two lead compounds Bz-Arg-Lys-D-Phg-NH
Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide
Terracciano, Stefania,Bruno, Ines,D'Amico, Elisabetta,Bifulco, Giuseppe,Zampella, Angela,Sepe, Valentina,Smith, Charles D.,Riccio, Raffaele
, p. 6580 - 6588 (2008/12/21)
In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a β-amino acid in the cyclopeptide backbone. Their biological profile is also described.
Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes
Kantharaju,Suresh Babu, Vommina V.
, p. 2152 - 2158 (2007/10/03)
An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth
A convenient method for the synthesis of β-amino acids via the Arndt-Eistert approach using p-toluenesulphonyl chloride as a carboxylic group activating agent
Vasanthakumar, Ganga-Ramu,Suresh Babu, Vommina V.
, p. 651 - 657 (2007/10/03)
A simple method for the synthesis of Z-/Boc-/Fmoc-protected β-amino acids by the Arndt-Eistert approach employing p-toluenesulphonyl chloride for the activation of the carboxyl group of Nα-protected amino acid is described. The method is rapid and gave good yields with opitical purity.
Convenient and simple synthesis of N-{[(9H-fluoren-9- yl)methoxy]carbonyl}-(Fmoc) protected β-amino acids (=homo-α-amino acids) employing Fmoc-α-amino acids and dicyclohexylcarbodiimide(DCC) mixtures
Ananda,Suresh Babu
, p. 418 - 423 (2007/10/03)
A simple approach for the homologation of α-amino acids to β-amino acids by the Arndt-Eistert method employing Fmoc-α-amino acid and N, N1- dicyclohexylcarbodiimide (DCC) mixture for the acylation of diazomethane, synthesizing the key intermediates Fmoc-α-amino acyldiazomethanes as crystalline solids is described.
Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted wolff rearrangement
Müller, Annett,Vogt, Carla,Sewald, Norbert
, p. 837 - 841 (2007/10/03)
A highly efficient protocol for Amdt-Eistert chain elongation of the base-labile fluorenylmethoxycarbonyl (Fmoc) protected α-amino acids by Ag+- catalyzed, ultrasound-promoted Wolff rearrangement of the corresponding α- diazo ketones at room temperature is described. The enantiomeric purity of the products was examined by capillary zone electrophoresis with chiral buffer systems.
