Boc-glycine methyl ester contains a glycine backbone bearing a methyl ester at the carboxyl terminus and an N-Boc (tert-butoxycarbonyl) protecting group on the amino functionality, classifying it as a protected amino acid ester. The molecule therefore presents a carbamate-protected primary amine and an esterified carboxyl group, with the Boc group serving to suppress undesired amine reactivity during peptide-coupling steps while the methyl ester provides a defined, non-zwitterionic handle for controlled transformations. It is employed as a peptide-synthesis building block and amino-acid-derivative intermediate in solution-phase or solid-phase strategies where stepwise assembly of protected residues and subsequent deprotection or ester modification are required.
CAT No: CP00904
CAS No:31954-27-5
Synonyms/Alias:Boc-Glycinemethylester;31954-27-5;Boc-Gly-OMe;N-(tert-Butoxycarbonyl)glycinemethylester;methyl2-[(tert-butoxycarbonyl)amino]acetate;N-Boc-glycineMethylEster;Methyl2-((tert-butoxycarbonyl)amino)acetate;PHUZOEOLWIHIKH-UHFFFAOYSA-N;MFCD00038267;Glycinemethylester,N-BOCprotected;methylN-(tert-butoxycarbonyl)glycinate;Methyl[(tert-butoxycarbonyl)amino]acetate;ST51038420;tert-Butoxycarbonylamino-aceticacidmethylester;PubChem21954;AC1LCUL8;BOCglycinemethylester;GLYCINE,TERT.BUTYLOXYCARBONYL,METHYLESTER;KSC493M0R;SCHEMBL523837;465674_ALDRICH;CTK3J3608;MolPort-001-764-523;ACN-S002350;STR09592
Boc-glycine methyl ester is a protected glycine derivative designed for peptide and peptidomimetic synthesis, featuring a Boc-protected amino group and a methyl ester at the carboxyl terminus. This structure makes it a practical building block for controlled coupling and downstream conversion of the ester into peptide-ready carboxylic acid derivatives. In synthetic workflows, the Boc group supports stepwise assembly strategies while the methyl ester provides a convenient protected handle for segment condensation and intermediate preparation.
1. Peptide Segment Coupling
Boc-glycine methyl ester is frequently used as a protected glycine building block in peptide synthesis workflows where a Boc-protected amino component is required for segment condensation. Peptide chemistry groups preparing short sequences or larger fragments rely on the methyl ester functionality to manage reactivity during assembly, followed by conversion to the corresponding carboxylic acid form when needed for subsequent coupling steps. This makes the reagent particularly useful in custom peptide manufacturing and research-grade peptide library construction, where consistent, protected reactivity is essential for reliable downstream processing.
2. Protected Intermediate Preparation
Boc-glycine methyl ester is also used as a versatile pharmaceutical intermediate in medicinal chemistry programs that require glycine-derived protected intermediates for further functionalization. Process development and synthesis teams often select this form to temporarily mask both the amine (via Boc) and the carboxyl group (via methyl ester), enabling selective transformations on other parts of a molecule without interference from free functional groups. The result is a convenient precursor for generating additional glycine-based fragments, including carboxyl-activated derivatives and selectively deprotected intermediates that feed into broader synthetic routes.
3. Solution-Phase and Fragment Synthesis
Boc-glycine methyl ester supports solution-phase and fragment-based peptide synthesis approaches used by research laboratories that prioritize modular assembly. Its protected amino group and esterified carboxyl group allow chemists to integrate glycine units into defined segments while maintaining compatibility with common peptide-building workflows used for assembling intermediates and final peptide targets. This reagent is particularly relevant when glycine must be introduced as a controlled, protected unit during iterative coupling and intermediate purification steps, such as in the preparation of peptide analogs for structure-activity relationship studies and chemical biology tool development.
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