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Synfacts 2022; 18(10): 1163
DOI: 10.1055/s-0041-1738581
Peptide Chemistry

(Diethylamino)sulfur Trifluoride (DAST) for Fmoc-Amino Acyl Fluoride Synthesis

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Kaduk C, *, Wenschuh H, Beyermann M, Forner K, Carpino LA, Bienert M. Institute of Molecular Pharmacology, Berlin, Germany
Synthesis of Fmoc-Amino Acid Fluorides via DAST, an Alternative Fluorinating Agent.

Lett. Pept. Sci. 1996;
2: 285-288
DOI: 10.1007/BF00142240.
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Key words

diethylaminosulfur trifluoride - coupling reagents - amino acyl fluorides - fluorination

Significance

The development of rapid, practically simple, and cost-effective methods for the synthesis of activated amino acids is a highly demanding field in the peptide industry. In 1996, Kaduk and co-workers reported a rapid and practically simple method for the conversion of Fmoc-amino acids into Fmoc-amino acyl fluorides with the help of (diethylamino)sulfur trifluoride.


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Comment

(Diethylamino)sulfur trifluoride (DAST) is one of the efficient reagents for the rapid conversion of Fmoc-amino acid into the corresponding Fmoc-amino acyl fluorides in good yields and with high purity. This method is practically simple and involves simple recrystallization or precipitation for the purification of Fmoc-amino acyl fluorides.


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Publication History

Article published online:
20 September 2022

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