Glycine benzyl ester hydrochloride

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Glycine benzyl ester hydrochloride
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A potent crosslinking inhibitor.

Inhibitors containing Unusual Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
Glycine benzyl ester hydrochloride
Gly-OBzl HClBenzyl glycinate hydrochloride; Benzyl glycinate hyd; N-Bn-glycine hydrochloride; benzyl glycinate; GLYCINE BENZYL ESTERHCI; GLY-OBZLCL
White powder
≥ 99% (HPLC)
1.132 g/cm3
Melting Point
138-140 °C
Boiling Point
245.5 °C at 760 mmHg
Store at 2-8 °C
1.A convenient route to N-[2-(Fmoc)aminoethyl]glycine esters and PNA oligomerization using a Bis-N-Boc nucleobase protecting group strategy.
Wojciechowski F1, Hudson RH. J Org Chem. 2008 May 16;73(10):3807-16. doi: 10.1021/jo800195j. Epub 2008 Apr 16.
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 (O(6)-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 O(6) 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.

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