Facile and Scalable Synthesis of Tripeptides with a Pro‐Pro Scaffold at C‐end: A TAG Approach,ChemistrySelect

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Facile and Scalable Synthesis of Tripeptides with a Pro‐Pro Scaffold at C‐end: A TAG Approach
ChemistrySelect ( IF 1.9 ) Pub Date : 2024-09-09 , DOI: 10.1002/slct.202402126
Akshitha D. Nagaraja ₁ , Veeranjaneyulu Avula _{1,

2} , H. S. Lalithamba ₃ , H. Surya Prakash Rao ₂ , Nagendra Govindappa ₁

Affiliation

The Pro‐Pro ligated tripeptides Ile‐Pro‐Pro 4 (IPP) and Val‐Pro‐Pro 5 (VPP) isolated from the fermented milk exhibit marked anti‐hypertension activity. Additionally, the naturally occurring Pro‐Pro ligated tripeptide Gly‐Pro‐Pro 6 (GPP) exhibits antioxidant properties. These peptides have enormous potential to be used as dilatory supplements. In the present study, we achieved a scalable, convenient, and high‐yielding synthesis of IPP, VPP, and GPP along with two more hydrophobic Pro‐Pro ligated tripeptides (APP 7, LPP 8) by employing the TAG technique. We used acid labile (2,4‐bis(octadecyloxy)phenyl)methanol as the TAG. We demonstrated synthesis of one of IPP at molar scale. We think that our method has the potential to be escalated to an industrial scale without much difficulty and they become available for general use as dietary supplements.

中文翻译：

在 C 端使用 Pro-Pro 支架轻松且可扩展地合成三肽：TAG 方法

从发酵乳中分离出的 Pro-Pro 连接三肽 Ile-Pro-Pro 4 (IPP) 和 Val-Pro-Pro 5 (VPP) 具有显着的抗高血压活性。此外，天然存在的 Pro-Pro 连接三肽 Gly-Pro-Pro 6 (GPP) 具有抗氧化特性。这些肽具有用作缓释补充剂的巨大潜力。在本研究中，我们通过采用 TAG 技术实现了 IPP、VPP 和 GPP 以及两种更疏水的 Pro-Pro 连接三肽（APP 7、LPP 8）的可扩展、方便和高产的合成。我们使用酸不稳定的（2,4-双（十八烷氧基）苯基）甲醇作为标签。我们展示了一种 IPP 在摩尔规模的合成。我们认为我们的方法有可能毫无困难地升级到工业规模，并且它们可以作为膳食补充剂广泛使用。

更新日期：2024-09-09

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