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Fmoc-DOPA(acetonide)-OH is an Fmoc-protected L-DOPA derivative in which the two adjacent catechol hydroxyl groups are masked together as an acetonide (cyclic acetal).
The protected catechol allows DOPA to be carried through peptide assembly with lower risk of uncontrolled oxidation or side reactions. After deprotection, the final DOPA residue provides the redox- and coordination-active catechol functionality characteristic of this noncanonical amino acid.
Product Information
| Product Name | Fmoc-DOPA(acetonide)-OH |
| Catalog No. | AS4184 |
| CAS No. | 852288-18-7 |
| Molecular Formula | C27H25NO6 |
| Molecular Weight | 459.50 g/mol |
| Building Block Type | Fmoc-protected L-DOPA with catechol acetonide protection |
| Primary Applications | DOPA-containing peptide synthesis; catechol peptide chemistry; adhesion and metal-binding research; noncanonical Fmoc-SPPS |
Why Protect the Catechol as an Acetonide
An unprotected catechol can oxidize to quinone-like species and can participate in metal binding or nonspecific side reactions. Acetonide protection masks both adjacent hydroxyls in one cyclic group during synthesis.
DOPA Chemistry Changes After Deprotection
Once the catechol is regenerated, pH, oxygen, redox conditions, metal ions, and nucleophiles can influence product behavior. We recommend planning handling and purification conditions for the final DOPA-containing peptide, not only for the protected monomer.
Applications Are Chemistry-Driven
DOPA-containing peptides are studied in adhesion, surface chemistry, redox processes, metal coordination, and biomimetic materials. The building block itself should not be described as having those functions until incorporated into the intended molecular system.
Procurement and QC
Confirm CAS 852288-18-7, C27H25NO6, MW 459.50 g/mol, L-DOPA stereochemistry, N-Fmoc protection, and catechol acetonide structure.
DOPA-containing sequences can require modified cleavage, oxidation control, and purification; these can be planned through custom modified peptide 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 acetonide protect?
It masks the two adjacent catechol hydroxyl groups of DOPA as a cyclic acetal.
Why protect the catechol?
Protection reduces uncontrolled oxidation and side reactions during synthesis.
Is the final DOPA catechol restored?
Yes, when the acetonide is removed under compatible deprotection conditions.
Related Technical Resources
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