Integrating 3,4-Dihydro-2H-1,4-oxazine into Peptides as a Modification: Silver Triflate-Catalyzed Cyclization of N-Propargyl N-Sulfonyl Amino Alcohols for SPPS Applications,Organic Letters

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Integrating 3,4-Dihydro-2H-1,4-oxazine into Peptides as a Modification: Silver Triflate-Catalyzed Cyclization of N-Propargyl N-Sulfonyl Amino Alcohols for SPPS Applications
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-03 , DOI: 10.1021/acs.orglett.4c02654
Abhijit Ramchandra Patil _{1,

2,

3} , Udaya Kiran Marelli _{1,

2,

3}

Affiliation

We present a methodology yielding 3,4-dihydro-2H-1,4-oxazine by cyclization of N-propargyl N-sulfonyl amino alcohols using silver triflate as a catalyst at ambient temperature. Additionally, we showcase the applicability of this methodology in solid phase peptide synthesis (SPPS) to introduce the oxazine heterocyclic ring into short peptides containing serine and threonine. Notably, Rink amide resin supported the on-resin formation of 3,4-dihydro-2H-1,4-oxazine, while 2-CTC resin facilitated the oxazine formation in a one-pot process involving peptide cleavage, deprotection, and subsequent C–O ring formation, thus offering a versatile method for the late-stage modification of peptides.

中文翻译：

将 3,4-二氢-2H-1,4-恶嗪整合到肽中作为修饰：三氟甲磺酸银催化 N-炔丙基 N-磺酰氨基醇的环化用于 SPPS 应用

我们提出了一种通过使用三氟甲磺酸银作为催化剂在环境温度下环化N-炔丙基N-磺酰基氨基醇来产生3,4-二氢-2H- 1,4-恶嗪的方法。此外，我们展示了该方法在固相肽合成（SPPS）中的适用性，将恶嗪杂环引入含有丝氨酸和苏氨酸的短肽中。值得注意的是，Rink 酰胺树脂支持 3,4-二氢-2 H -1,4-恶嗪在树脂上形成，而 2-CTC 树脂则在一锅法中促进恶嗪的形成，涉及肽裂解、脱保护和后续反应。 C-O环的形成，从而为肽的后期修饰提供了一种通用的方法。

更新日期：2024-09-03

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