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Boc-D-Arg(Pbf)-OH is a D-arginine derivative with Boc protection on the α-amino group and Pbf protection on the guanidino side chain. Pbf suppresses guanidino reactivity while the D stereocenter provides the intended noncanonical backbone configuration.
For a conventional Fmoc/tBu route, consider Fmoc-D-Arg(Pbf)-OH. The side-chain protection is comparable, but the temporary N-protection and synthesis workflow differ.
Product Information
| Product Name | Boc-D-Arg(Pbf)-OH |
| Catalog No. | AS2021 |
| CAS No. | 186698-61-3 |
| Molecular Formula | C24H38N4O7S |
| Molecular Weight | 526.65 g/mol |
| Building Block Type | Nα-Boc-Nω-Pbf-D-arginine |
| Primary Applications | D-arginine peptide synthesis; stereochemical SAR; Boc-compatible protected chemistry; Pbf-protected guanidino route development |
Why D-Arg Is a Distinct Experimental Variable
D-arginine preserves a strongly basic guanidino side chain while reversing α-carbon stereochemistry. This can alter protease recognition, peptide conformation, transport, and target binding; effects should be measured in the completed peptide.
Pbf Protects the Guanidino Group
Pbf is an acid-labile sulfonyl protecting group widely used to control arginine side-chain reactivity. It remains on the guanidino group during protected synthesis and is removed under appropriately strong acidic deprotection conditions.
Boc Versus Fmoc for the Same D-Arg/Pbf Residue
The final deprotected residue can be D-Arg in either case, but Boc and Fmoc define different temporary protection cycles. Boc-D-Arg(Pbf)-OH is therefore most useful in Boc-compatible or solution-phase routes rather than as a direct substitute in standard Fmoc automation.
Procurement and QC
Confirm CAS 186698-61-3, C24H38N4O7S, MW 526.65 g/mol, D/(2R) stereochemistry, Nα-Boc protection, and Nω-Pbf guanidino protection. Mass alone cannot prove D versus L identity.
Researchers comparing L/D arginine substitutions can also review the current D-Form Amino Acids portfolio; complete sequences can be produced through custom synthesis.
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
What does Pbf protect?
Pbf protects the arginine guanidino side chain.
How does Boc-D-Arg(Pbf)-OH differ from Fmoc-D-Arg(Pbf)-OH?
They install the same D-Arg/Pbf residue but use different α-amino protecting groups and deprotection strategies.
Can mass spectrometry confirm D stereochemistry?
No. D and L enantiomers have the same molecular mass.
Related Technical Resources
Discuss D-amino-acid custom peptide synthesis