67398-29-2Relevant academic research and scientific papers
High-performance liquid chromatographic enantioseparation of N-aryl-thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide-based chiral stationary phases
Drabowicz, Józef,Kudzin, Marcin H.,Kudzin, Zbigniew H.,Pokora-Sobczak, Patrycja
supporting information, p. 131 - 140 (2017/12/28)
The first successful enantioseparation of representative O,O-diphenyl-N-arylthioureidoalkylphosphonates, (±)-Ptc-ValP(OPh)2 & (±)-Ptc-LeuP(OPh)2 and thiourylenedi(isobutyl phosphonate), Tcm[ValP(OPh)2]2 on analytical and semipreparative scale was achieved by high-performance liquid chromatography using polysaccharide-based chiral stationary phases (CPs). Atc-AAP(OPh)2 was obtained using modified tricomponent condensations of the corresponding aldehydes, N-arylthiourea and triphenyl phosphite whereas Tcm[ValP(OPh)2]2 by the condensations of aldehydes, thiourea, and triphenyl phosphite. The prepared, racemic (±)-Atc-AAP(OPh)2 [(±)-Ptc-ValP(OPh)2, (±)-Ptc-LeuP(OPh)2, (±)-Ptc-PglyP(OPh)2 and (±)-Ntc-PglyP(OPh)2] and racemic (±)-Tcm[AAP(OPh)2]2 [(±)-Tcm[NvaP(OPh)2]2 & (±)-Tcm[ValP(OPh)2]2] were adequately characterized and used for chromatographic separations on high-performance liquid chromatography–chiral stationary phases. The best results were obtained for (±)-Ptc-ValP(OPh)2, (±)-Ptc-LeuP(OPh)2 and (±)-Tcm[ValP(OPh)2]2.
Efficient synthesis of phosphonodepsipeptides derived from norleucine
Pícha, Jan,Budě?ínsky, Milo?,Han?lová, Ivona,?anda, Miloslav,Fiedler, Pavel,Vaněk, Václav,Jirá?ek, Ji?í
experimental part, p. 6090 - 6103 (2011/03/18)
In the present work, we describe in detail an efficient solution synthesis of norleucine-derived phosphonopeptides mimicking the peptide sequences Nle-Gly(Ala) and Nle-Gly(Ala)-Val. The most efficient strategy involved use of the benzyl group. The synthesis was achieved through BOP-catalysed coupling of the monobenzyl ester of the N-Cbz-protected phosphonate derivative of norleucine with the hydroxyl moieties of derivatised l-lactic or glycolic acid. Subsequently, complete deprotection of the products was achieved in good yields by one-step Pd-catalysed hydrogenolysis. We also prepared the Fmoc-Nle-Ψ[PO(OH)O]-CH2-COOH synthon and demonstrated that this precursor is a suitable building block for the solid-phase synthesis of cysteine-containing phosphonopeptides.
Synthesis of norleucine-derived phosphonopeptides
Pícha, Jan,Budě?ínsky, Milo?,?anda, Miloslav,Jirá?ek, Ji?í
, p. 4366 - 4368 (2008/12/21)
The synthesis of norleucine-derived phosphonopeptides was achieved by BOP-catalyzed coupling of the monobenzyl ester of a N-CBz-protected phosphonate derivative of norleucine with hydroxyl moieties of derivatized lactic or glycolic acids. The complete deprotection of the product esters/carbamates was achieved in good yields by one-step Pd-catalyzed hydrogenolysis.
