N-Me-allo-Ile-OBzl · p-tosylate is an N-methylated allo-isoleucine amino acid derivative featuring an isoleucine-derived carbon skeleton and an O-benzyl ester (OBzl) at the carboxyl terminus, with a p-toluenesulfonate counterion associated with the molecule. The amino functionality is present as an N-methyl amide-type substitution (N-Me) while the side chain bears the characteristic branched aliphatic functionality of isoleucine, and the benzyl-protected carboxyl group and tosylate salt form are designed to control chemoselectivity and solubility during handling and stepwise synthesis. In peptide-chemistry and chemical biology workflows, this protected, salt-associated amino acid building block is used as a precursor for preparing more complex amino acid and peptide derivatives, including incorporation of N-methylated, allo-configured residues and generation of intermediates bearing a protected carboxyl group for subsequent coupling or labeling strategies.
CAT No: CP26719
CAS No:201544-39-0
Synonyms/Alias:201544-39-0;(2S,3R)-Benzyl3-methyl-2-(methylamino)pentanoate4-methylbenzenesulfonate;CTK8B7657;MolPort-023-331-070;N-Me-allo-Ile-OBzl.p-tosylate;ANW-58088;AKOS016003030;AK-88948;RT-023417
N-Me-allo-Ile-OBzl · p-tosylate is an N-methylated allo-isoleucine derivative presented as a benzyl ester and paired with a p-toluenesulfonate counterion, combining a chiral amino acid framework with an activated leaving-group functionality. The allo stereochemistry relative to the isoleucine backbone defines the spatial arrangement of the α-amino substituent and the side-chain branching, which can influence peptide coupling geometry and downstream stereochemical outcomes. The benzyl ester masks the carboxylate to enable controlled deprotection strategies, while the N-methyl group reduces free amine reactivity and can steer selective transformations. The tosylate component provides an anionic counterion associated with a sulfonate leaving group, supporting salt formation and enabling compatibility with standard amino acid derivative handling in synthetic and process contexts.
1. Protected Amino Acid Chemistry
N-Me-allo-Ile-OBzl · p-tosylate is used in protected amino acid synthesis workflows where benzyl ester masking supports carboxyl-group control during peptide building block preparation. The N-methylated allo-isoleucine core maintains a defined stereocenter while limiting unprotected amine chemistry, which can be advantageous when orthogonal protection and selective activation are required. The tosylate counterion can facilitate salt-form stability and predictable handling of the amino acid derivative during coupling setup and intermediate purification. Downstream, the compound can serve as a chiral amino acid intermediate that feeds into iterative protection/deprotection sequences to reach peptide-ready forms for amide bond construction.
2. Peptide Coupling Synthesis
N-Me-allo-Ile-OBzl · p-tosylate is applicable to peptide synthesis planning where a benzyl-protected carboxyl group and a stereodefined allo-isoleucine residue support controlled assembly of peptide bonds. The side-chain architecture of isoleucine, together with the N-methyl substitution, can be leveraged to generate N-methylated peptide segments or peptidomimetic motifs that require reduced backbone hydrogen-bonding. The protected ester can be converted to a reactive carboxylate equivalent under deprotection/activation strategies compatible with common peptide coupling chemistries. The resulting N-methyl allo-isoleucine residue can be incorporated into linear peptides and protected peptide fragments to probe sequence effects and stereochemical influence on folding-relevant conformations.
3. Peptidomimetics And SAR Studies
N-Me-allo-Ile-OBzl · p-tosylate is suitable for peptidomimetic construction and structure-activity relationship studies where N-methyl amino acid incorporation modulates conformational preferences and proteolytic stability proxies. The allo stereochemistry, combined with the branched isoleucine side chain, enables systematic variation of stereochemical and steric parameters in peptide analog libraries. The benzyl ester functionality supports stepwise synthesis of constrained fragments, allowing preparation of analogs where the carboxyl terminus is introduced or revealed at a controlled stage. The tosylate-associated salt form can support consistent intermediate handling when producing multiple analogs for SAR-driven comparison of backbone modifications.
4. Chiral Intermediate For Derivatization
N-Me-allo-Ile-OBzl · p-tosylate functions as a chiral amino acid intermediate for stereoselective derivatization routes that require retention or controlled inversion at the allo-defined stereocenter. The N-methyl group and benzyl ester provide orthogonality that can be exploited to selectively transform side-chain or terminal functionalities while deferring backbone-level changes. The sulfonate pairing supports formation of a well-defined ionic form that can improve reproducibility in synthetic sequences for downstream functional group installation. The compound can be converted into additional chiral building blocks, including activated carboxyl derivatives and protected amide-forming intermediates, supporting fine chemical synthesis and stereochemical library generation.
5. Pharmaceutical Intermediate Preparation
N-Me-allo-Ile-OBzl · p-tosylate is relevant to pharmaceutical intermediate preparation where amino acid-derived fragments are assembled into protected building blocks for later coupling and deprotection. The benzyl ester provides a standard carboxyl protection handle that can be removed under conditions compatible with sensitive functional groups present in multi-step manufacturing routes. The N-methylated allo-isoleucine motif can be incorporated into peptide-like intermediates to support controlled backbone substitution patterns used in process chemistry for complex molecule assembly. The tosylate counterion supports salt-based handling and can be integrated into batch-to-batch workflows for producing chiral intermediates used in downstream active-ingredient synthesis.
6. Specialty Chemical Manufacturing
N-Me-allo-Ile-OBzl · p-tosylate can be employed in specialty chemical production where amino acid ester and N-methylated chiral fragments are required for manufacturing of functionalized peptide analogs and related materials. The combination of a protected carboxyl group (benzyl ester) and a controlled amine state (N-methyl) supports predictable intermediate conversion into amide-linked structures without premature side reactions. The branched isoleucine side chain contributes hydrophobic character that can influence solubility and polymer/biomaterial compatibility when amino acid-derived monomers or crosslinking fragments are constructed from similar scaffolds. The compound's chiral, protected structure aligns with industrial chemical manufacturing needs for reproducible synthesis of amino acid-based intermediates used in applied product development.
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