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Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids

A number of protected proline‐containing dipeptides Boc‐Xaa‐Pro‐OBut were converted via epimerization‐free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc‐Xaa‐Glp‐OBut. The latter were subjected to oxidative Hoffman‐type rearrangement induced by PhI[OC(O)CF3]2 to gi...

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Published in:	Journal of peptide science 2005-03, Vol.11 (3), p.175-186
Main Authors:	Chulin, A. N., Rodionov, I. L., Baidakova, L. K., Rodionova, L. N., Balashova, T. A., Ivanov, V. T.
Format:	Article
Language:	English
Subjects:	aminoacyl incorporation reaction Aminoacylation Aminobutyrates - chemistry dilactams Glutamic Acid - analogs & derivatives Glutamic Acid - chemical synthesis Glutamic Acid - chemistry Hoffman rearrangement Molecular Structure Ornithine - chemistry Oxidation-Reduction Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry PIFA pyroglutamic acid Pyrrolidonecarboxylic Acid - chemistry ring expansion ruthenium tetroxide
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description	A number of protected proline‐containing dipeptides Boc‐Xaa‐Pro‐OBut were converted via epimerization‐free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc‐Xaa‐Glp‐OBut. The latter were subjected to oxidative Hoffman‐type rearrangement induced by PhI[OC(O)CF3]2 to give N‐(aminoacyl)‐pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10‐membered‐ring dilactams derived from 1,4‐diaminobutyric and glutamic acids in practicable yields. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.
doi_str_mv	10.1002/psc.611
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The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10‐membered‐ring dilactams derived from 1,4‐diaminobutyric and glutamic acids in practicable yields. 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N.</creatorcontrib><creatorcontrib>Rodionov, I. L.</creatorcontrib><creatorcontrib>Baidakova, L. K.</creatorcontrib><creatorcontrib>Rodionova, L. N.</creatorcontrib><creatorcontrib>Balashova, T. A.</creatorcontrib><creatorcontrib>Ivanov, V. T.</creatorcontrib><title>Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids</title><title>Journal of peptide science</title><addtitle>J. Peptide Sci</addtitle><description>A number of protected proline‐containing dipeptides Boc‐Xaa‐Pro‐OBut were converted via epimerization‐free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc‐Xaa‐Glp‐OBut. The latter were subjected to oxidative Hoffman‐type rearrangement induced by PhI[OC(O)CF3]2 to give N‐(aminoacyl)‐pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10‐membered‐ring dilactams derived from 1,4‐diaminobutyric and glutamic acids in practicable yields. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.</description><subject>aminoacyl incorporation reaction</subject><subject>Aminoacylation</subject><subject>Aminobutyrates - chemistry</subject><subject>dilactams</subject><subject>Glutamic Acid - analogs & derivatives</subject><subject>Glutamic Acid - chemical synthesis</subject><subject>Glutamic Acid - chemistry</subject><subject>Hoffman rearrangement</subject><subject>Molecular Structure</subject><subject>Ornithine - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>PIFA</subject><subject>pyroglutamic acid</subject><subject>Pyrrolidonecarboxylic Acid - chemistry</subject><subject>ring expansion</subject><subject>ruthenium tetroxide</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNqFkV2L1TAQhoso7rqK_0BypRfaY6ZNP3IpB3dVVj2gondhmkzXaL9M0tX-HP-pqT3olQiBSZiH983MmyT3ge-A8-zp5PWuBLiRnAKXMoW8rm6u96pIsxKqk-SO9184j72ivJ2cQFHmRSnq0-TnwdGEDoMdB4aDYY5QB3ttw8LGlmFvhxH10rFpceNVNwfsMZDfsXPUtiPmlyF8Jm_9SgNPe-obcmRSZ4crphfdWc2MnWgK1pBnhpy9JsNaN_YMnojU2N8ezRwWF9H1C5vN-tDW-LvJrRY7T_eO9Sz5cP78_f5Fevn24uX-2WWq81pASgYbaqEl5DVHjFPLkmRVYQsStBYkheSxK0AayrOSWiykkaKp8jozQuRnycNNd3Ljt5l8UL31mroOBxpnr8pKxJP_H8wAhMgERPDRBmo3eu-oVZOzPbpFAVdrbCrGpmJskXxwlJybnsxf7phTBB5vwPe49OVfOurwbr_JpRttfaAff2h0X-MUeVWoj28uVCY-8eLV64PK8l-5HbMx</recordid><startdate>200503</startdate><enddate>200503</enddate><creator>Chulin, A. 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subjects	aminoacyl incorporation reaction Aminoacylation Aminobutyrates - chemistry dilactams Glutamic Acid - analogs & derivatives Glutamic Acid - chemical synthesis Glutamic Acid - chemistry Hoffman rearrangement Molecular Structure Ornithine - chemistry Oxidation-Reduction Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry PIFA pyroglutamic acid Pyrrolidonecarboxylic Acid - chemistry ring expansion ruthenium tetroxide
title	Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids
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