Beta-methylcysteines : synthesis and application in native chemical ligation /
Native chemical ligation has emerged as a powerful method in peptide synthesis. In this method, an initial transthioesterification step involves a chemoselective reaction that occurs between a peptide fragment containing an amino-terminal cysteine residue and a second peptide fragment containing a c...
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| Format: | Thesis eBook |
| Language: | English |
| Published: |
[Place of publication not identified] :
[publisher not identified] ;
2000.
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| Subjects: | |
| Online Access: | Link to OAKTrust copy |
| Summary: | Native chemical ligation has emerged as a powerful method in peptide synthesis. In this method, an initial transthioesterification step involves a chemoselective reaction that occurs between a peptide fragment containing an amino-terminal cysteine residue and a second peptide fragment containing a carboxyl-terminal thioester group, leading to an S-acyl intermediate. A subsequent S->N acyl migration forms a native amide bond. Of the translatable amino acids, only cysteine has the requisite β-mercapto substituent. However, the method could in principle be extended to other amino acids through the use of a temporary sulfhydryl, which could be removed post-ligation with Ra-Ni. To explore this possibility, we prepared the diastereomeric β-methylcysteines (thiothreonines). The suitability of these reagents for native chemical ligation was discussed, and efforts toward improved and general stereoselective syntheses of β-substituted cysteines was discussed. |
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| Item Description: | "Major subject: Chemistry". In title Greek letter Beta is a symbol Vita. |
| Physical Description: | ix, 74 leaves : illustrations ; 28 cm. Also available online. Issued also on microfiche from Lange Micrographics. |
| Bibliography: | Includes bibliographical references (leaves 28-30). |