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Synfacts 2021; 17(09): 1065
DOI: 10.1055/s-0040-17119950
Peptide Chemistry

Trimethylaluminum-Mediated Peptide Synthesis

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Martin SF, *, Dwyer MP, Lynch CL. The University of Texas at Austin, USA
Application of AlMe3-Mediated Amidation Reactions to Solution Phase Peptide Synthesis.

Tetrahedron Lett. 1998;
39: 1517-1520
DOI: 10.1016/S0040-4039(98)00071-9.
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Key words

trimethylaluminum - solution-phase synthesis - peptide coupling - unprotected amino acids

Significance

The amide bond is ubiquitous; in particular, it is present in the backbones of peptides and in many natural products. Consequently, it has gained considerable importance in organic synthesis. Chemists are therefore continually searching for new methods for amide and/or peptide bond-forming reactions. In 1998, Martin and co-workers invented an AlMe3-mediated peptide synthesis from unprotected amino acids in the solution phase.


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Comment

This inexpensive AlMe3-mediated solution-phase amide bond forming reaction proceeds smoothly to afford the desired products in moderate to good yields. The method can also be applied in syntheses of tripeptides in moderate yields.


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Publication History

Article published online:
18 August 2021

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