1028077-29-3

Upstream product

• 1028077-23-7 allyl N-[2-((fluorenylmethoxycarbonyl)amino)ethyl]-N-[(N²,N²-bis(tert-butoxycarbonyl)-O⁶-benzylguanin-9-yl)acetyl]glycinate 

Relevant academic research and scientific papers

A convenient route to N-[2-(Fmoc)aminoethyl]glycine esters and PNA oligomerization using a bis-N-Boc nucleobase protecting group strategy

(Chemical Equation Presented) A simple and practical synthesis of the benzyl, allyl, and 4-nitrobenzyl esters of N-[2-(Fmoc)aminoethyl]glycine is described starting from the known N-(2-aminoethyl)glycine. These esters are stored as stable hydrochloride salts and were used in the synthesis of peptide nucleic acid monomers possessing bis-N-Boc-protected nucleobase moieties on the exocyclic amino groups of ethyl cytosin-1-ylacetate, ethyl adenin-9-ylacetate and ethyl (O6-benzylguanin-9-yl)acetate. Upon ester hydrolysis, the corresponding nucleobase acetic acids were coupled to N-[2-(Fmoc)aminoethyl] glycine benzyl ester or to N-[2-(Fmoc)aminoethyl]glycine allyl ester in order to retain the O6 benzyl ether protecting group of guanine. The Fmoc/bis-N-Boc-protected monomers were successfully used in the Fmoc-mediated solid-phase peptide synthesis of mixed sequence 10-mer PNA oligomers and are shown to be a viable alternative to the currently most widely used Fmoc/Bhoc-protected peptide nucleic acid monomers.