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Efficient Syntheses of Naphthoquinone-Dipeptides
(Thieme, 2010) Sakhuja, Rajeev
Naphthoquinone-dipeptides are synthesized in 76-89% yield from naphthoquinone-amino acid conjugates by N-acylbenzotriazole methodology in aqueous media at 20 ˚C
Traceless reductive ligation at a tryptophan site: a facile access to β-hydroxytryptophan appended peptides
(RSC, 2016) Sakhuja, Rajeev; Bajaj, Kiran
An efficient methodology for cysteine-free ligation at a tryptophan (Trp) site is described. A chemically active scaffold, β-hydroxy-α-azidotryptophan, has been synthesized and explored towards the synthesis of a series of β-hydroxytryptophan appended native peptides in good yields via one-pot reductive traceless ligation of β-O-peptidyl-α-azidotryptophan involving an O → N peptidyl transfer strategy. Pre-organized conformational analysis and reaction energy pathway based theoretical studies further supported the experimental findings on the chemical structure stability of ligated products.