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Constrained Dipeptide Surrogates: 5- and 7-Hydroxy Indolizidin-2-one Amino Acid Synthesis from Iodolactonization of Dehydro-2,8-diamino Azelates.


ABSTRACT: The constrained dipeptide surrogates 5- and 7-hydroxy indolizidin-2-one N-(Boc)amino acids have been synthesized from L-serine as a chiral educt. A linear precursor ∆4-unsaturated (2S,8S)-2,8-bis[N-(Boc)amino]azelic acid was prepared in five steps from L-serine. Although epoxidation and dihydroxylation pathways gave mixtures of hydroxy indolizidin-2-one diastereomers, iodolactonization of the ∆4-azelate stereoselectively delivered a lactone iodide from which separable (5S)- and (7S)-hydroxy indolizidin-2-one N-(Boc)amino esters were synthesized by sequences featuring intramolecular iodide displacement and lactam formation. X-ray analysis of the (7S)-hydroxy indolizidin-2-one N-(Boc)amino ester indicated that the backbone dihedral angles embedded in the bicyclic ring system resembled those of the central residues of an ideal type II' β-turn indicating the potential for peptide mimicry.

SUBMITTER: Mulamreddy R 

PROVIDER: S-EPMC8746717 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Constrained Dipeptide Surrogates: 5- and 7-Hydroxy Indolizidin-2-one Amino Acid Synthesis from Iodolactonization of Dehydro-2,8-diamino Azelates.

Mulamreddy Ramakotaiah R   Lubell William D WD  

Molecules (Basel, Switzerland) 20211223 1


The constrained dipeptide surrogates 5- and 7-hydroxy indolizidin-2-one <i>N</i>-(Boc)amino acids have been synthesized from L-serine as a chiral educt. A linear precursor ∆<sup>4</sup>-unsaturated (2<i>S</i>,8<i>S</i>)-2,8-bis[<i>N</i>-(Boc)amino]azelic acid was prepared in five steps from L-serine. Although epoxidation and dihydroxylation pathways gave mixtures of hydroxy indolizidin-2-one diastereomers, iodolactonization of the ∆<sup>4</sup>-azelate stereoselectively delivered a lactone iodid  ...[more]

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