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Boc-D-Phe-OH is the Boc-protected D-enantiomer of phenylalanine. It retains the aromatic benzyl side chain of Phe while reversing α-carbon stereochemistry relative to the natural L residue.
For Fmoc-based workflows, the corresponding building block is Fmoc-D-Phe-OH. The residue introduced is D-Phe in both cases, but the temporary N-protection and route compatibility are different.
Product Information
| Product Name | Boc-D-Phe-OH |
| Catalog No. | AS2030 |
| CAS No. | 18942-49-9 |
| Molecular Formula | C14H19NO4 |
| Molecular Weight | 265.30 g/mol |
| Building Block Type | Boc-protected D-phenylalanine |
| Primary Applications | D-amino-acid peptide synthesis; stereochemical SAR; Boc/solution-phase peptide chemistry; protease-stability studies |
D-Phe as a Stereochemical Probe
D-Phe substitution can alter local peptide conformation, protease recognition and target binding while preserving an aromatic side chain. The effect is position-specific and should be measured in the final peptide.
Boc Versus Fmoc Route Logic
Boc is acid-labile, whereas Fmoc is base-labile. Boc-D-Phe-OH therefore fits Boc-oriented and selected solution-phase routes rather than being directly interchangeable with the Fmoc derivative.
Mass Cannot Confirm D Stereochemistry
Boc-D-Phe and Boc-L-Phe have identical formula and molecular mass. We consider the correct CAS, structure and chiral documentation essential when stereochemical interpretation is part of the experiment.
Procurement and QC
PubChem confirms CAS 18942-49-9, formula C14H19NO4 and MW 265.30 g/mol for N-Boc-D-phenylalanine. Confirm D configuration on the lot-specific COA.
Peptides containing partial or all-D substitutions can be produced through custom peptide synthesis with D-amino acids.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.
Frequently Asked Questions
Can MW distinguish D-Phe from L-Phe?
No. Enantiomers have identical molecular mass.
Why choose Boc-D-Phe-OH instead of Fmoc-D-Phe-OH?
The choice depends on the route's temporary N-protection strategy.
What is D-Phe used for in peptide research?
It is used to probe stereochemical recognition, conformation and proteolytic stability.
Related Technical Resources
Read how D-amino acids expand peptide design