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CBZ-OSu (Z-OSu) is N-(benzyloxycarbonyloxy)succinimide, an activated succinimidyl carbonate used to introduce the benzyloxycarbonyl (Cbz or Z) protecting group onto amines. It is widely used in amino-acid, peptide and organic synthesis when a hydrogenolysis-removable amine protecting group is desired.
Compared with direct use of benzyl chloroformate (Cbz-Cl), Z-OSu provides an activated N-hydroxysuccinimide-derived carbonate route for Cbz transfer and can be useful for selective amine protection in complex synthetic intermediates.
Product Information
| Product Name | CBZ-OSu(Z-OSu) |
| Preferred Names | Cbz-OSu; Z-OSu; N-(Benzyloxycarbonyloxy)succinimide |
| Catalog No. | AS2003 |
| CAS No. | 13139-17-8 |
| Molecular Formula | C12H11NO5 |
| Molecular Weight | 249.22 g/mol |
| Transferred Group | Cbz / Z (benzyloxycarbonyl) |
| Primary Use | Selective protection of amino groups |
Cbz Protection in Peptide Chemistry
The Cbz/Z group protects an amine as a benzyl carbamate. Unlike Fmoc, which is normally removed under basic conditions, and Boc, which is acid-labile, Cbz is commonly removed by catalytic hydrogenolysis when the rest of the molecule is compatible with hydrogenation conditions.
This distinct deprotection mechanism makes Cbz useful in orthogonal protection strategies where acid- and base-labile groups must remain intact.
Cbz-OSu vs Fmoc-OSu
Fmoc-OSu and Cbz-OSu are both activated succinimidyl carbonates, but they transfer different protecting groups. Fmoc is base-labile; Cbz is typically hydrogenolysis-labile.
The reagents are therefore not interchangeable in a protection scheme even though their activated-carbonate chemistry is conceptually similar.
Application Scope
Applications include protection of amino acids and amines, preparation of protected peptide building blocks, orthogonal protecting-group strategies, aminoglycoside modification and synthesis of specialty organic intermediates.
The reagent is a synthetic protection reagent and is not intended for direct in vitro or in vivo assays.
Safety and Procurement Considerations
Supplier hazard classifications are not fully uniform for CAS 13139-17-8. A conservative current classification used in this Alan Scientific MSDS is H315, H319 and H335; actual lot documentation should be aligned with the upstream supplier safety data.
Confirm CAS 13139-17-8, Cbz/Z transfer identity, molecular formula, assay and lot-specific COA. Do not confuse standard Cbz-OSu with brominated Z(2-Br)-OSu or Fmoc-OSu.
Product Documents
A Material Safety Data Sheet (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 protecting group does Cbz-OSu install?
It installs the benzyloxycarbonyl group, commonly abbreviated Cbz or Z.
How is Cbz usually removed?
Cbz is commonly removed by catalytic hydrogenolysis when the substrate is compatible with those conditions.
Is Cbz-OSu the same as Fmoc-OSu?
No. They transfer different protecting groups with different deprotection mechanisms.
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