172169-88-9Relevant articles and documents
Total Chemical Synthesis of an Intra-A-Chain Cystathionine Human Insulin Analogue with Enhanced Thermal Stability
Karas, John A.,Patil, Nitin A.,Tailhades, Julien,Sani, Marc-Antoine,Scanlon, Denis B.,Forbes, Briony E.,Gardiner, James,Separovic, Frances,Wade, John D.,Hossain, Mohammed Akhter
supporting information, p. 14743 - 14747 (2016/11/23)
Despite recent advances in the treatment of diabetes mellitus, storage of insulin formulations at 4 °C is still necessary to minimize chemical degradation. This is problematic in tropical regions where reliable refrigeration is not ubiquitous. Some degradation byproducts are caused by disulfide shuffling of cystine that leads to covalently bonded oligomers. Consequently we examined the utility of the non-reducible cystine isostere, cystathionine, within the A-chain. Reported herein is an efficient method for forming this mimic using simple monomeric building blocks. The intra-A-chain cystathionine insulin analogue was obtained in good overall yield, chemically characterized and demonstrated to possess native binding affinity for the insulin receptor isoform B. It was also shown to possess significantly enhanced thermal stability indicating potential application to next-generation insulin analogues.
An alternative solid-phase approach to C1-oxytocin
Mayer, John P.,Heil, James R.,Zhang, Jingwen,Munson, Mark C.
, p. 7387 - 7390 (2007/10/02)
A general, solid-phase method based on in situ formation of a cystathionine residue is described. The procedure allows for the introduction of a thioether moiety in place of a native disulfide bond and is illustrated here by the synthesis of C1-oxytocin 1.