Boc-L-Phenylalanine methyl ester is a protected amino acid ester derived from L-phenylalanine, featuring a benzyl side chain attached to the alpha carbon and a methyl ester at the carboxyl terminus. The molecule bears an N-Boc (tert-butoxycarbonyl) protecting group on the amino functionality, which masks the primary amine and controls chemoselectivity during peptide-coupling steps, while the ester form presents a carboxyl group equivalent suitable for controlled transformations. In synthesis, it functions as a stepwise building block for preparing peptides and peptide intermediates in protected amino acid strategies, where the combination of Boc protection and methyl ester functionality supports sequential assembly and downstream conversion to carboxyl-reactive derivatives as needed.
CAT No: CP01612
CAS No:51987-73-6
Synonyms/Alias:Boc-Phe-OMe;51987-73-6;Boc-L-phenylalaninemethylester;L-Boc-phenyl-alaninemethylester;N-Boc-L-phenylalaninemethylester;N-(tert-Butoxycarbonyl)-L-phenylalaninemethylester;(S)-methyl2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-PHENYL-PROPIONICACIDMETHYLESTER;(L)-Boc-phenyl-alaninemethylester;PubChem13507;SCHEMBL84524;KSC595E1R;Boc-phenylalaninemethylester;421707_ALDRICH;15179_FLUKA;CTK4J5218;MolPort-000-861-467;SDSWSVBXRBXPRL-LBPRGKRZSA-N;ACT04980;ZINC2555042;ZINC02555042;AM82170;AS06714;AJ-39681;AK-40356
Boc-L-Phenylalanine methyl ester is a Boc-protected L-phenylalanine derivative in which the carboxyl group is esterified as a methyl ester, providing a stable, non-zwitterionic building block for peptide assembly and intermediate synthesis. The benzyl side chain of phenylalanine supports incorporation into hydrophobic peptide segments, while the Boc group establishes an N-protected amino functionality compatible with protected-amino-acid workflows. This protected ester format is commonly selected when downstream coupling requires controlled reactivity and reliable handling of the amino acid backbone.
1. Solid-Phase Peptide Building
Boc-L-Phenylalanine methyl ester is used as a protected amino acid building block for constructing peptide sequences where phenylalanine residues are required with a Boc-protected amino terminus. Researchers performing custom peptide synthesis and peptide library development rely on this protected format to manage chemoselectivity during stepwise assembly, particularly when phenylalanine's hydrophobic side chain is needed to tune peptide solubility, folding propensity, or binding-site interactions. The methyl ester functionality supports preparation of defined peptide segments or segment precursors prior to final coupling and purification.
2. Protected Segment Intermediates
Boc-L-Phenylalanine methyl ester serves as a practical intermediate for preparing defined protected peptide fragments and amino acid derivatives used in solution-phase peptide synthesis. Medicinal chemistry groups and peptide process developers often choose this form to standardize the phenylalanine unit with a Boc-protected nitrogen and an esterified carboxyl group, enabling controlled downstream transformations during fragment condensation and purification. The ester handle is particularly useful in workflows where a segment precursor must be generated and carried through multi-step assembly with minimized side reactions.
3. Pharmaceutical Peptide Intermediate Development
Boc-L-Phenylalanine methyl ester is frequently employed in the development of peptide-based pharmaceutical intermediates, including precursors used to generate larger, protected constructs for subsequent deprotection and final assembly. Peptide chemistry teams in industrial and translational research settings use this derivative to reliably introduce a phenylalanine residue into manufacturing-relevant intermediate streams, supporting reproducible synthesis of sequence-defined materials. The combination of Boc protection on the amino group and methyl ester protection on the carboxyl group helps maintain stability and handling consistency across intermediate stages.
4. Analytical Reference Material Preparation
Boc-L-Phenylalanine methyl ester is also used to prepare analytical standards and method development materials for confirming identity and monitoring protected-amino-acid handling in peptide chemistry workflows. Analytical laboratories working with LC methods for protected building blocks, intermediate purity checks, or reaction progress monitoring may use this compound as a reference point for retention behavior and fragmentation patterns associated with Boc-protected phenylalanine derivatives. Its defined protected structure makes it useful when validating analytical procedures that track protected intermediates during peptide synthesis and fragment assembly.
3. Implications of ligand-receptor binding kinetics on GLP-1R signalling
5. TMEM16F and dynamins control expansive plasma membrane reservoirs
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More