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Synthetic Route to Human Relaxin-2 via Iodine-Free Sequential Disulfide Bond Formation

Synthetic Route to Human Relaxin-2 via Iodine-Free Sequential Disulfide Bond Formation

Organic Letters 18(21): 5516-5519

A new synthetic route to human relaxin-2 has been established through a sequential disulfide bond formation process in the absence of iodine. It is enabled by a combination of cysteine protection with penicillin G acylase-labile Phacm and a newly identified thiol activator bis(5-(2-methoxyethoxy)-2-pyrimidinyl disulfide. The long-standing challenges in relaxin B-chain assembly and its poor solubility have been solved by the insertion of two isoacyl dipeptide segments. The overall yield was 25% from the B chain and 5.8% from the B-chain starting resin.

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Accession: 058960016

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PMID: 27754694

DOI: 10.1021/acs.orglett.6b02751

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