Boc-His(1-Mts)-OH · DCHA is a Boc-protected histidine derivative bearing a 1-methylthioethyl (Mts) substituent on the imidazole ring, classifying it as a protected, side-chain-modified amino acid building block for peptide chemistry. The molecule contains a Boc carbamate protecting group on the amino functionality and a free carboxylic acid, while the imidazole N-substitution with the Mts group provides a thioether-containing side-chain handle that can be manipulated under appropriate conditions, with stereochemistry not specified in the name. As a salt-associated protected amino acid (DCHA), it is used in stepwise peptide synthesis and related chemical biology workflows where controlled chemoselectivity and side-chain functional modulation are required for preparing histidine-containing peptides or amino acid derivatives for labeling and structure-activity studies.
CAT No: CP26165
CAS No:105931-56-4
Synonyms/Alias:Boc-His(Tau-Mts)-OH · DCHA
Boc-His(1-Mts)-OH · DCHA is a protected histidine building block used for peptide and peptidomimetic synthesis, featuring an N-terminal Boc protecting group and a side-chain protection strategy based on 1-Mts (methanesulfonyl-type) protection. The presence of DCHA (dicyclohexylamine) indicates formation of a defined salt form that is commonly selected to improve handling and facilitate consistent coupling workflows in peptide chemistry. This reagent is typically employed by peptide synthesis groups that require controlled histidine side-chain chemistry during assembly of sequences where histidine reactivity must be masked until the desired deprotection stage.
1. Solid-Phase Peptide Synthesis
Boc-His(1-Mts)-OH · DCHA is frequently used by custom peptide synthesis teams and peptide reagent users to incorporate histidine residues into sequences on solid support while maintaining side-chain protection throughout chain elongation. The Boc group supports standard N-protection/deprotection cycles used in protected-amino-acid strategies, while the 1-Mts side-chain protection helps minimize undesired side reactions of histidine during coupling and washing steps. This form is particularly useful when the final peptide requires histidine to remain chemically controlled until the end of synthesis, supporting downstream purification and characterization workflows.
2. Solution-Phase Segment Coupling
Boc-His(1-Mts)-OH · DCHA is also applied in solution-phase peptide synthesis and segment condensation, where histidine must remain protected during activation and coupling of peptide fragments. Researchers assembling longer constructs or using modular fragment strategies often select this protected histidine derivative to reduce variability caused by histidine side-chain reactivity under coupling conditions. The DCHA salt form is commonly chosen in development settings to support reproducible reagent dosing and improved solid-handling behavior, which can be important for scale-up of peptide intermediates and for preparing defined segments for subsequent assembly.
3. Histidine-Containing Peptide Libraries
Boc-His(1-Mts)-OH · DCHA supports peptide library construction where systematic variation around histidine-containing motifs is required, such as in structure-activity relationship studies of histidine-rich peptides or peptidomimetic scaffolds. By using a protected histidine building block, library workflows can standardize coupling steps and preserve side-chain integrity across multiple parallel syntheses. This approach is valuable for medicinal chemistry groups that need consistent peptide intermediates for rapid screening and for analytical teams that require reproducible histidine incorporation to enable reliable LC-MS and purification comparisons across library members.
4. Pharmaceutical Intermediate Development
Boc-His(1-Mts)-OH · DCHA is used in the preparation of peptide-based pharmaceutical intermediates and advanced intermediates for process development, where protected amino acid building blocks are required to control functional-group compatibility during multistep synthesis. Development chemists rely on such protected histidine derivatives to manage chemoselectivity during assembly of peptide fragments that later undergo global deprotection and purification. The defined salt form supports practical manufacturing-style handling of the amino acid reagent, helping maintain consistent feedstock behavior during intermediate preparation and enabling more predictable downstream processing of histidine-containing constructs.
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