Zinc-promoted simple synthesis of oligomer-free N(alpha)-Fmoc-amino acids using Fmoc-Cl as an acylating agent under neutral conditions.
A range of N(alpha)-Fmoc-protected amino acids, including those that contain t-butyl moiety, have been synthesized by employing Fmoc-Cl utilizing the activated, commercial zinc dust-promoted synthesis of carbamates under neutral conditions. A general procedure is described that circumvents the oligomerization side reaction normally noticed in Schotten-Baumann conditions. It is a simple, convenient and clean method. Thus, Fmoc-amino acids are obtained in high yield (85-92%) and purity as checked by thin-layer chromatography, high-performance liquid chromatography and other physical methods.
Gopi
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HN
Department of Studies in Chemistry, Bangalore University, India.
Suresh Babu
V V
VV
D000215:Acylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015032:Zinc
D000596:Amino Acids; D002219:Carbamates; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D015032:Zinc