Bringing Macrolactamization Full Circle: Self-Cleaving Head-to-Tail Macrocyclization of Unprotected Peptides via Mild N‑Acyl Urea Activation

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Bringing Macrolactamization Full Circle: Self-Cleaving Head-to-Tail Macrocyclization of Unprotected Peptides via Mild N‑Acyl Urea Activation

Arbour, Christine A; Belavek, Kayla J; Tariq, Rooha; Mukherjee, Subha; Tom, Janine K; Isidro-Llobet, Albert; Kopach, Michael E; Stockdill, Jennifer L

Journal of organic chemistry, 01/2019, Letnik: 84, Številka: 2

Journal Article

We establish herein conditions for the cyclization of unprotected N-acyl urea-linked peptides to form macrocyclic peptides mediated by N-terminal cysteine. We report a detailed investigation of the parameters of the reaction, including variation of the reaction conditions, the C-terminal residue, and the macrocycle size. C-Terminal epimerization was not observed. The synthesis of macrocyclic targets ranging from tetrapeptides to the disulfide-linked 14-mer, sunflower trypsin inhibitor 1 are demonstrated. For most substrates, hydrolysis and head-to-tail dimer formation are avoided.

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Dostop do baze podatkov JCR je dovoljen samo uporabnikom iz Slovenije. Vaš trenutni IP-naslov ni na seznamu dovoljenih za dostop, zato je potrebna avtentikacija z ustreznim računom AAI.

Leto	Faktor vpliva		Izdaja		Kategorija		Razvrstitev
Leto	JCR	SNIP	JCR	SNIP	JCR	SNIP	JCR	SNIP

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