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(S)-Boc-γ-Iodo-Abu-OMe is a protected 4-iodo-2-aminobutyric acid derivative. The alpha-amino group is Boc-protected, the carboxyl group is a methyl ester and the terminal gamma carbon carries iodine as a leaving group.
The terminal iodide is the defining synthetic handle. It enables substitution or intramolecular reaction chemistry that is not available from ordinary Abu, while Boc and methyl ester protection keep the amino acid under orthogonal control.
Product Information
| Product Name | (S)-Boc-γ-Iodo-Abu-OMe |
| Catalog No. | AS2093 |
| CAS No. | 101650-14-0 |
| Molecular Formula | C10H18INO4 |
| Molecular Weight | 343.16 g/mol |
| Building Block Type | Boc-protected gamma-iodo amino-acid methyl ester |
| Primary Applications | Noncanonical amino-acid synthesis; nucleophilic substitution; intramolecular cyclization; linker and heterocycle precursor chemistry |
Why the Gamma-Iodide Is Useful
Iodide is a good leaving group, making the terminal carbon suitable for substitution by selected nucleophiles. This allows the reagent to serve as a precursor to sulfur-, nitrogen- or oxygen-substituted amino-acid analogs and to some cyclic or constrained scaffolds.
Boc and Methyl Ester Protection
Boc masks the amino group under many neutral or basic transformations, while the methyl ester prevents the carboxyl group from participating in unintended reactions. The deprotection order should be planned around the functionality installed through the iodide.
Stereochemistry Must Be Preserved
The product is S-configured at the alpha carbon. Nucleophilic chemistry at the gamma carbon does not by itself change that stereocenter, but route conditions can still affect overall chemical integrity. We recommend confirming optical identity when the intermediate is used to generate a new noncanonical residue.
Where It Fits in Building-Block Design
This reagent is best viewed as a precursor for creating additional amino-acid chemistry rather than as a routine SPPS monomer. For broader context, see noncanonical amino acids in peptide discovery.
Procurement and QC Considerations
Confirm CAS 101650-14-0, C10H18INO4, MW 343.16 g/mol and S configuration. Because organic iodides can degrade or discolor during storage, lot appearance and purity should be reviewed before using the material in low-yield substitution chemistry.
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 is the main reactive handle?
The terminal gamma-iodide is the principal leaving group for substitution chemistry.
Is the carboxyl group free?
No. It is protected as a methyl ester.
Is this used directly in routine Fmoc-SPPS?
It is more commonly used as an intermediate for preparing specialized noncanonical amino-acid derivatives.
Related Technical Resources
Browse specialty peptide building blocks
Review noncanonical residue design