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Influence of Sulfur‐Containing Diamino Acid Structure on Covalently Crosslinked Copolypeptide Hydrogels
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-09-17 , DOI: 10.1002/asia.201801031 Eric D. Raftery 1 , Eric G. Gharkhanian 1 , Nicole G. Ricapito 2 , J. McNamara 2 , Timothy J. Deming 3
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-09-17 , DOI: 10.1002/asia.201801031 Eric D. Raftery 1 , Eric G. Gharkhanian 1 , Nicole G. Ricapito 2 , J. McNamara 2 , Timothy J. Deming 3
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Biologically occurring non‐canonical di‐α‐amino acids were converted into new di‐N‐carboxyanhydride (di‐NCA) monomers in reasonable yields with high purity. Five different di‐NCAs were separately copolymerized with tert‐butyl‐l‐glutamate NCA to obtain covalently crosslinked copolypeptides capable of forming hydrogels with varying crosslinker density. Comparison of hydrogel properties with residue structure revealed that different di‐α‐amino acids were not equivalent in crosslink formation. Notably, l‐cystine was found to produce significantly weaker hydrogels compared to l‐homocystine, l‐cystathionine, and l‐lanthionine, suggesting that l‐cystine may be a sub‐optimal choice of di‐α‐amino acid for preparation of copolypeptide networks. The di‐α‐amino acid crosslinkers also provided different chemical stability, where disulfide crosslinks were readily degraded by reduction, and thioether crosslinks were stable against reduction. This difference in response may provide a means to fine tune the reduction sensitivity of polypeptide biomaterial networks.
中文翻译：
含硫二氨基酸结构对共价交联共多肽水凝胶的影响
生物产生的非规范二α-氨基酸以合理的收率和高纯度转化为新的二氮-羧基酸酐（di-NCA）单体。五个不同的二种NCA分别用共聚叔丁基-升-谷氨酸NCA，以获得能够形成具有变化的密度的交联剂水凝胶的共价交联共聚。比较水凝胶性质和残基结构，发现不同的二-α-氨基酸在交联形成中不相等。值得注意的是，升-cystine发现相比以产生显著弱凝胶升-homocystine，升-cystathionine，和升-lanthionine，表明升在制备共肽网络时，胱氨酸可能不是最佳的二α-氨基酸选择。二α-氨基酸交联剂还提供不同的化学稳定性，其中二硫键容易被还原降解，硫醚交联对还原稳定。这种响应差异可以提供一种手段来微调多肽生物材料网络的还原敏感性。
更新日期：2018-09-17
中文翻译：
含硫二氨基酸结构对共价交联共多肽水凝胶的影响
生物产生的非规范二α-氨基酸以合理的收率和高纯度转化为新的二氮-羧基酸酐（di-NCA）单体。五个不同的二种NCA分别用共聚叔丁基-升-谷氨酸NCA，以获得能够形成具有变化的密度的交联剂水凝胶的共价交联共聚。比较水凝胶性质和残基结构，发现不同的二-α-氨基酸在交联形成中不相等。值得注意的是，升-cystine发现相比以产生显著弱凝胶升-homocystine，升-cystathionine，和升-lanthionine，表明升在制备共肽网络时，胱氨酸可能不是最佳的二α-氨基酸选择。二α-氨基酸交联剂还提供不同的化学稳定性，其中二硫键容易被还原降解，硫醚交联对还原稳定。这种响应差异可以提供一种手段来微调多肽生物材料网络的还原敏感性。
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