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Synfacts 2021; 17(08): 0951
DOI: 10.1055/s-0040-1706268
Peptide Chemistry

Zinc Dust Mediated Peptide Synthesis from Fmoc-Amino Acid Chlorides and Amino Acid Hydrochlorides

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Gopi HN, Suresh Babu VV. * Bangalore University, India
Synthesis of Peptides Employing Fmoc-Amino Acid Chlorides and Commercial Zinc Dust.

Tetrahedron Lett. 1998;
39: 9769-9772
DOI: 10.1016/S0040-4039(98)02169-8.
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Key words

zinc catalysis - Fmoc-amino acid chlorides - amino acids - amidation

Significance

The construction of peptide bonds is one of the most essential and widely encountered chemical transformations in organic synthesis. In general, coupling of Fmoc-amino acid chlorides with amino acid esters requires the use of an aqueous inorganic base or an organic base. The use of these bases can cause severe issues of epimerization or cleavage of the Fmoc group. In 1998, Gopi and Suresh Babu developed a method for peptide synthesis from Fmoc-amino acid chlorides and amino acid hydrochloride salts mediated by commercially available zinc dust.


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Comment

The zinc-mediated peptide coupling of Fmoc-amino acid chlorides with amino acid hydrochloride salts proceeds quickly and affords the desired peptides in high yields. This protocol is straightforward in practice, racemization free, and avoids side reactions.


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Publication History

Article published online:
20 July 2021

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