Cyclen-Containing Inhibitors of Carboxypeptidase A Synthesized in Search of Target-Selective Artificial Proteases

Song, Jung Bae; Hah, Sang Soo; Suh, Junghun

doi:10.5012/bkcs.2004.25.11.1703

Cited by 3 publications

(1 citation statement)

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“…The phosphonodepsidipeptide 17 was synthesized via the coupling of methyl N-Cbz-1-aminoethylphosphonochloridate (13b) generated from phosphonic monomethyl ester 12b and methyl (S)-2-hydroxy-3-phenylpropanoate (18) followed by hydrogenolysis. It was further coupled to cyclen to afford various cyclen-containing phosphonodepsipeptides as inhibitors of carboxypeptidase A (Scheme 2) [20].…”

Section: Synthesis Of α-Phosphonodepsipeptidesmentioning

confidence: 99%

Synthetic strategies of phosphonodepsipeptides

Xu¹

2021

Beilstein J. Org. Chem.

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Phosphonodepsipeptides are phosphorus analogues of depsipeptides and phosphonate-linked analogues of naturally occurring peptides. They are more stable than phosphonopeptides and have been widely applied as enzyme inhibitors, haptens for the production of antibodies, biological agents, and prodrugs. The synthetic strategies towards phosphonodepsipeptides are reviewed, including the phosphonylation of hydroxy esters with phosphonochloridates, the condensation of phosphonic monoesters and hydroxy esters, the alkylation of phosphonic monoesters with 1-(alkoxycarbonyl)alkyl halides or sulfonates, multicomponent condensation of amides, aldehydes, and dichlorophosphites followed by alcoholysis with hydroxy esters, the phosphinylation of hydroxy esters with phosphonochloridites followed by oxidation, and the carbene insertion of N-protected amino acids with 1-diazoalkylphosphonates. This review includes the synthesis of α-, β-, and γ-phosphonodepsipeptides and phosphonodepsipeptides with C-1-hydroxyalkylphosphonic acids.

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Section: Synthesis Of α-Phosphonodepsipeptidesmentioning

confidence: 99%

Synthetic strategies of phosphonodepsipeptides

Xu¹

2021

Beilstein J. Org. Chem.

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Cyclen‐Containing Inhibitors of Carboxypeptidase A Synthesized in Search of Target‐Selective Artificial Proteases.

2005

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Eight title compounds of type (I) or (II) are prepared as diastereomeric mixtures which can be separated by HPLC. The Cu(II) and Co(III) complexes of the isomers of (I) and (II) with the longer elution time contain an effective binding site for carboxypeptidase A (CPA) as well as the peptide-cleaving catalytic center, but they fail to cleave the peptide backbone of CPA. -(SONG, J. B.; HAH, S. S.; SUH*, J.; Bull. Korean Chem.

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