BOC

BOC

Synthesis of Bioactive Peptides for Pharmaceutical Applications

Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019

Jaison Jeevanandam, Ashish Kumar Solanki, Shailza Sharma, Prabir Kumar Kulabhusan, Sapna Pahil, Michael K. Danquah

The variation in SPPS lies in the protecting groups, matrix and coupling reagents used; and methodology used to synthesize and cleave the final peptide from the matrix. Generally, chemical synthesis uses two protocols such as Boc and Fmoc which is named on the basis of the protecting group type used for the protection of the tert-butyl and sensitive Nα-amino group of certain amino acid side chains (David and Luis, 2001). The differences in the two protocols are depicted in Table 6.1.

Amino acids: Building blocks for the synthesis of greener amphiphiles

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Journal Information

Published in Journal of Dispersion Science and Technology, 2018

Nausheen Joondan, Sabina Jhaumeer Laulloo, Prakashanand Caumul

The amino group is generally protected using BOC or methyl groups prior to the formation of the amide derivative. Amide-based surfactants (Figure 6) have been prepared by the reaction of N-protected amino acids with an equimolar amount of straight or branched chain alkylamines in the presence of coupling reagents such as DCC/dimethylamino pyridine (DMAP)[42] or 1-hydroxybenzotriazole (HOBT)/N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC-HCl),[43] followed by deprotection to give the desired amide surfactants. The free amino group can then be quaternised with excess methyl halide in the presence of anhydrous potassium carbonate and 18-crown-6-ether to yield the QUATS 31–35.[42,43]

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Synthesis of Bioactive Peptides for Pharmaceutical Applications

Amino acids: Building blocks for the synthesis of greener amphiphiles