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Synfacts 2021; 17(02): 0229
DOI: 10.1055/s-0040-1706108
Peptide Chemistry

Dipeptides Synthesis by Using Phosphazene Bases to Enhance the Solubility of Amino Acids

Contributor(s):
Hisashi Yamamoto
,
An Wu
Palomo C, *, Palomo AL, *, Palomo F, Mielgo A. Universidad del País Vasco, Apartado, Spain
Soluble α-Amino Acid Salts in Acetonitrile: Practical Technology for the Production of Some Dipeptides.

Org. Lett. 2002;
4: 4005-4008
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Key words

amino acids - phosphazene bases - ketone esters - dipeptides - solubilization

Significance

α-Amino acids are widely used in organic chemistry. However, the low solubility of free amino acids causes some problems in organic synthesis. In 2002, a method to enhance the solubility of amino acids in organic media by using phosphazene bases was reported.


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Comment

Some dipeptides can be synthesized from free amino acids in acetonitrile when phos­phazene bases are used to increase solubility. The yields of the target peptides are excellent. This strategy might be useful in other reactions involving α-amino acids.


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Publication History

Article published online:
20 January 2021

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