脱氢氨基酸的 N-保护依赖性磷酸化：磷氨基酸和短肽的简便合成。

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-11-20 DOI:10.1002/asia.202401244

Pranay Kothuri, Haripriya Bhumannagari, Shravani Battula, Kolachina Rekha, Kiranmai Nayani

{"title":"脱氢氨基酸的 N-保护依赖性磷酸化：磷氨基酸和短肽的简便合成。","authors":"Pranay Kothuri, Haripriya Bhumannagari, Shravani Battula, Kolachina Rekha, Kiranmai Nayani","doi":"10.1002/asia.202401244","DOIUrl":null,"url":null,"abstract":"An efficient Mn(III)-promoted phosphorylation of dehydroalanine (Dha) has been developed to give unusual α-amino acids bearing phosphonates/phosphine oxides and β-vinyl phosphonates/phosphinates depending on N-protection of amino acid. N,N-diprotected dehydroalanine reacted with H-phosphonates and H-phosphine oxides to give structurally diverse phosphorylated α-amino acids through conjugate addition of phosphorous radical generated by Mn(OAc)3.2H2O. Whereas, a highly Z-selective phosphorylation was observed in the case of mono N-Boc protected dehydroalanine via cross dehydrogenative coupling to give (Z)- β -vinyl phosphono amino acid. The method is successfully applied to short peptides to derive unusual phosphono-peptides under mild conditions.","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202401244"},"PeriodicalIF":3.5000,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"N-Protection Dependent Phosphorylation of Dehydroamino Acids: Facile Synthesis of Phosphono- Amino Acids and Short Peptides.\",\"authors\":\"Pranay Kothuri, Haripriya Bhumannagari, Shravani Battula, Kolachina Rekha, Kiranmai Nayani\",\"doi\":\"10.1002/asia.202401244\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An efficient Mn(III)-promoted phosphorylation of dehydroalanine (Dha) has been developed to give unusual α-amino acids bearing phosphonates/phosphine oxides and β-vinyl phosphonates/phosphinates depending on N-protection of amino acid. N,N-diprotected dehydroalanine reacted with H-phosphonates and H-phosphine oxides to give structurally diverse phosphorylated α-amino acids through conjugate addition of phosphorous radical generated by Mn(OAc)3.2H2O. Whereas, a highly Z-selective phosphorylation was observed in the case of mono N-Boc protected dehydroalanine via cross dehydrogenative coupling to give (Z)- β -vinyl phosphono amino acid. The method is successfully applied to short peptides to derive unusual phosphono-peptides under mild conditions.\",\"PeriodicalId\":145,\"journal\":{\"name\":\"Chemistry - An Asian Journal\",\"volume\":\" \",\"pages\":\"e202401244\"},\"PeriodicalIF\":3.5000,\"publicationDate\":\"2024-11-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry - An Asian Journal\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1002/asia.202401244\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202401244","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

研究人员开发了一种高效的锰(III)促进的脱氢丙氨酸（Dha）磷酸化反应，根据氨基酸的 N-保护，可得到不同寻常的α-氨基酸，其中含有膦酸盐/膦氧化物和β-乙烯基膦酸盐/膦氧化物。通过 Mn(OAc)3.2H2O 产生的磷自由基的共轭加成，N,N-二保护的脱氢丙氨酸与 H-膦酸盐和 H-膦氧化物反应，得到结构多样的磷酸化 α-氨基酸。而在单 N-Boc 保护的脱氢丙氨酸中，通过交叉脱氢偶联观察到了高度的 Z 选择性磷酸化，得到了 (Z)-β -乙烯基膦酰基氨基酸。该方法成功地应用于短肽，在温和的条件下衍生出不寻常的膦酰肽。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

N-Protection Dependent Phosphorylation of Dehydroamino Acids: Facile Synthesis of Phosphono- Amino Acids and Short Peptides.

An efficient Mn(III)-promoted phosphorylation of dehydroalanine (Dha) has been developed to give unusual α-amino acids bearing phosphonates/phosphine oxides and β-vinyl phosphonates/phosphinates depending on N-protection of amino acid. N,N-diprotected dehydroalanine reacted with H-phosphonates and H-phosphine oxides to give structurally diverse phosphorylated α-amino acids through conjugate addition of phosphorous radical generated by Mn(OAc)3.2H2O. Whereas, a highly Z-selective phosphorylation was observed in the case of mono N-Boc protected dehydroalanine via cross dehydrogenative coupling to give (Z)- β -vinyl phosphono amino acid. The method is successfully applied to short peptides to derive unusual phosphono-peptides under mild conditions.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).