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Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides.

ABSTRACT: The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral ?-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered ?-substituted hydrazino acid residues.

SUBMITTER: Kang CW 

PROVIDER: S-EPMC4201324 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Solid-phase synthesis of tetrahydropyridazinedione-constrained peptides.

Kang Chang Won CW   Ranatunga Sujeewa S   Sarnowski Matthew P MP   Del Valle Juan R JR  

Organic letters 20141008 20

The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained  ...[more]

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