$100.00 - $285.71
Fmoc-L-Glu-OBzl is Nalpha-Fmoc-L-glutamic acid alpha-benzyl ester. The alpha amino group is Fmoc-protected and the alpha carboxyl is protected as a benzyl ester, leaving the side-chain gamma carboxyl group free.
That protection map is the central feature of this product. It is not the conventional Fmoc-Glu(OtBu)-OH pattern used for routine alpha-peptide-chain elongation. Instead, it provides access to side-chain-selective glutamate chemistry, including gamma-amide or gamma-glutamyl derivative preparation.
Product Information
| Product Name | Fmoc-L-Glu-OBzl |
| Catalog No. | AS2116 |
| CAS No. | 122350-52-1 |
| Molecular Formula | C27H25NO6 |
| Molecular Weight | 459.49 g/mol |
| Chemical Identity | Nalpha-Fmoc-L-glutamic acid alpha-benzyl ester (Fmoc-Glu-OBzl) |
| Building Block Type | Regioselectively protected glutamic-acid derivative |
| Primary Applications | Gamma-carboxyl derivatization, gamma-glutamyl chemistry and protected glutamate intermediate synthesis |
Why the Alpha-Benzyl Ester Matters
Protecting the alpha carboxyl prevents it from being activated while leaving the gamma carboxyl available. This reverses the usual reactivity expected from a standard peptide monomer and enables selective side-chain coupling. We consider exact carboxyl protection the first identity check for this SKU because the abbreviated “OBzl” name alone does not tell an inexperienced purchaser which glutamate carboxyl is esterified.
A Useful Route to Gamma-Glutamyl Derivatives
The free side-chain acid can be activated and coupled to an amine while the alpha amino and alpha carboxyl remain protected. Subsequent deprotection can then expose the functions needed for further chemistry. This can be useful for gamma-linked glutamate fragments and other regioselective glutamic-acid derivatives.
How This Changes SPPS Planning
Because the alpha carboxyl is benzyl-protected, Fmoc-L-Glu-OBzl is not a direct drop-in replacement for standard Fmoc-Glu side-chain-protected monomers in routine chain elongation. The protection logic should be mapped against the intended sequence using the SPPS guide for Fmoc protection and coupling strategy before ordering.
Procurement and QC Considerations
Confirm CAS 122350-52-1, C27H25NO6 and MW 459.49 g/mol. PubChem and major supplier records identify this material specifically as the alpha-benzyl ester. We recommend verifying the drawn structure on the COA because alpha- versus gamma-ester protection would produce different synthetic behavior even if shorthand naming is similar.
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
Which glutamate carboxyl group is benzyl-protected in Fmoc-L-Glu-OBzl?
The alpha carboxyl is the benzyl ester; the side-chain gamma carboxyl remains free.
Is this the same protection pattern as Fmoc-Glu(OtBu)-OH?
No. Standard Fmoc-Glu(OtBu)-OH protects the side-chain carboxyl and leaves the alpha carboxyl available for peptide coupling; Fmoc-L-Glu-OBzl does the opposite at the carboxyl functions.
What is the free gamma carboxyl useful for?
It can be activated for side-chain-selective coupling, including preparation of gamma-glutamyl or other glutamate side-chain derivatives.
Related Technical Resources
Review the Fmoc-SPPS workflow and protecting-group strategy.
Discuss a gamma-linked or selectively modified glutamate peptide project.