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Your search keyword '"Elbatrawi, Yassin M."' showing total 9 results
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2. Total Synthesis of Pargamicin A

Author

Elbatrawi, Yassin M., primary, Gerrein, Taylor, additional, Anwar, Avraz, additional, Makwana, Kamlesh M., additional, Degen, David, additional, Ebright, Richard H., additional, and Del Valle, Juan R., additional

Published
2022
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4. Diastereoselective Synthesis of (3 R ,5 R)-γ-Hydroxypiperazic Acid.

Author

Gerrein, Taylor A., Elbatrawi, Yassin M., and Del Valle, Juan R.

Subjects
*ASYMMETRIC synthesis, *ACIDS, *HYDROXYLATION, *PEPTIDES
Abstract

We report an asymmetric synthesis of the (3 R ,5 R)-γ-hydroxypiperazic acid (γ-OHPiz) residue encountered in several bioactive nonribosomal peptides. Our strategy relies on a diastereoselective enolate hydroxylation reaction and electrophilic N-amination to provide the acyclic γ-OHPiz precursor. This orthogonally protected α-hydrazino acid intermediate is amenable to late-stage diazinane ring formation following incorporation into a peptide chain. We determined the N-terminal amide rotamer propensity of the γ-OHPiz residue and showed that the γ-OH substituent enhances trans -amide bias relative to piperazic acid. [ABSTRACT FROM AUTHOR]

Published
2021
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