Sequential α-Ketoacid-Hydroxylamine (KAHA) Ligations: Synthesis of C-Terminal Variants of the Modifier Protein UFM1

3 for 3: Sequential α‐ketoacid–hydroxylamine (KAHA) ligations with 5‐oxaproline allow access to the modifier protein UFM1 (Ubiquitin‐fold modifier 1) with a C‐terminal amide, carboxylic acid, or a masked thioester. Fmoc protection of an N‐terminal 5‐oxaproline permits the assembly of proteins of >...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-09, Vol.51 (38), p.9693-9697
Main Authors: Ogunkoya, Ayodele O., Pattabiraman, Vijaya R., Bode, Jeffrey W.
Format: Article
Language:English
Subjects:
amides
chemoselectivity
Hydroxylamine - chemistry
ligation reactions
Models, Molecular
Molecular Structure
Proline - analogs & derivatives
Proline - chemistry
protein synthesis
proteins
Ubiquitins - chemical synthesis
Ubiquitins - chemistry
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Summary:3 for 3: Sequential α‐ketoacid–hydroxylamine (KAHA) ligations with 5‐oxaproline allow access to the modifier protein UFM1 (Ubiquitin‐fold modifier 1) with a C‐terminal amide, carboxylic acid, or a masked thioester. Fmoc protection of an N‐terminal 5‐oxaproline permits the assembly of proteins of >80 residues in good yield by a two‐pot process from three readily prepared medium‐sized protein segments.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201204144