Boc-2,5-Dimethy-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing additional methyl substituents at the 2- and 5-positions of the side-chain aromatic ring and a D-configuration at the α-carbon as indicated by the name. The molecule contains a Boc-protected α-amino group and a free carboxylic acid, with the substituted phenyl side chain providing hydrophobic character and steric modulation relative to unsubstituted phenylalanine. As a Boc-protected amino acid suitable for stepwise coupling, it is employed in peptide synthesis and structure-activity studies to introduce a sterically and electronically modified aromatic residue while maintaining chemoselectivity through the Boc protecting group.
CAT No: CP14005
Boc-2,5-Dimethy-D-Phenylalanine is a Boc-protected, stereodefined amino acid building block featuring a D-configuration at the alpha carbon and a sterically enhanced, dimethyl-substituted side chain on the aromatic phenylalanine scaffold. This non-proteinogenic, conformationally biased residue is commonly used in peptide and peptidomimetic synthesis to probe structure-property relationships and to introduce steric and hydrophobic effects while maintaining a protected amino functionality for controlled coupling. The Boc group supports routine protected-amino-acid workflows, making the compound a practical intermediate for assembling modified peptide segments and medicinal chemistry leads.
1. Peptidomimetic Building Blocks
Boc-2,5-Dimethy-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to incorporate a sterically constrained, D-configured aromatic residue into peptidomimetic scaffolds. The 2,5-dimethyl substitution pattern on the phenyl ring provides a distinct hydrophobic steric profile relative to standard phenylalanine, which is valuable for structure-activity relationship studies where side-chain bulk and aromatic substitution are tuned to influence conformation and local interactions. Researchers typically select this Boc-protected form to streamline segment assembly in custom peptide synthesis workflows and to keep the amino functionality masked until coupling steps are performed.
2. Modified Peptide Synthesis
Boc-2,5-Dimethy-D-Phenylalanine supports the synthesis of modified peptides where non-natural amino acid incorporation is used to control residue-level properties. Peptide synthesis teams use this protected building block to introduce a D-amino acid stereocenter and a substituted phenyl side chain that can alter backbone geometry preferences and side-chain packing within the growing sequence. Because the molecule is supplied as a Boc-protected amino acid, it fits established protected-amino-acid coupling strategies used for solution-phase or segment-based peptide construction, enabling consistent incorporation of the same stereodefined residue across analog series.
3. Structure-Property SAR Studies
Boc-2,5-Dimethy-D-Phenylalanine is frequently employed in SAR campaigns that require systematic variation of aromatic side-chain substitution and stereochemistry. Chemical biology and medicinal chemistry teams use this residue to generate analog panels in which steric bulk and aromatic substitution are varied while keeping other parts of the scaffold constant, supporting direct comparisons of how these changes affect chemical behavior and molecular recognition trends in downstream assays. The D-configuration and the 2,5-dimethyl pattern make the building block particularly useful when researchers aim to distinguish stereochemical and steric contributions from backbone effects, using a well-defined, protected amino acid intermediate for reproducible synthesis.
4. Pharmaceutical Intermediate Development
Boc-2,5-Dimethy-D-Phenylalanine is also used as a defined chiral intermediate in the development of peptide-like drug candidates and specialized chemical entities that rely on non-natural amino acid residues. Process and development chemists value the protected Boc functionality and stereodefined D-configuration because it provides a controlled entry point for later functionalization steps within a larger synthetic route. In this context, the compound serves as a reliable building block for preparing modified fragments that can be assembled into larger intermediates, enabling consistent downstream manufacturing of research quantities for lead optimization and analog generation.
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