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New observations on peptide bond formation using CDMT

✍ Scribed by Christine E. Garrett; Xinglong Jiang; Kapa Prasad; Oljan Repič

Book ID
104251172
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
128 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The optimized formation of the peptide bond by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) has been found to occur rapidly and essentially quantitatively in a one-pot, one-step procedure. This new method is effective for the coupling of a variety of reactive partners, including chiral amino acids (e.g. N-acetyl-L-leucine) without significant loss of configuration. Significant racemization was observed when the typical literature conditions were used, due to the formation of an azlactone intermediate which is configurationally unstable under the reaction conditions. A simpler, precipitative workup procedure is also disclosed in this report.

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