Boc-O-methyl-L-Serinedicyclohexylamine salt is a protected, amino acid derivative in which the serine side chain is O-methylated and the α-amino group is masked as a Boc carbamate, while the carboxyl functionality is present as a dicyclohexylamine salt. The molecule therefore contains both Boc-protected amino and carboxylate salt forms, with the O-methyl substituent on the side-chain hydroxyl replacing the free alcohol and providing a less hydrogen-bonding, more ether-like functionality for subsequent peptide chemistry. In peptide synthesis and related derivatization workflows, the Boc group supports chemoselective handling of the α-amino functionality, and the salt form can improve physical handling and enable controlled conversion to activated carboxyl derivatives for stepwise coupling.
CAT No: CP01816
CAS No:51293-47-1
Synonyms/Alias:51293-47-1;Boc-O-Methyl-L-Serine;(S)-2-((tert-Butoxycarbonyl)amino)-3-methoxypropanoicacid;BOC-SER(ME)-OH;(S)-2-(tert-butoxycarbonylamino)-3-methoxypropanoicacid;(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxypropanoicacid;BOC-SER(ME)-OHDCHA;AmbotzBAA5080;Boc-O-Methyl-L-Ser;N-Boc-O-methyl-serine;AC1Q44JD;SCHEMBL580779;CTK8B4547;MolPort-006-705-867;RFGMSGRWQUMJIR-LURJTMIESA-N;C21H40N2O5;ACT10774;ZINC2526267;ANW-45439;(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicAcid;AKOS015899843;Boc-O-methyl-L-Serinedicyclohexylamine;CB-1701;RP27189;N-tert-Butoxycarbonyl-O-methyl-L-serine
Boc-O-methyl-L-Serinedicyclohexylamine salt is a Boc-protected serine derivative where the side-chain hydroxyl is methylated (O-methyl), and the amino acid is supplied as a dicyclohexylamine salt to improve handling and formulation for peptide chemistry. This protected, stereodefined building block is designed for incorporation into protected peptide intermediates, enabling controlled functional-group management during sequential coupling and later deprotection steps. Its combination of a Boc N-terminus and an O-methyl side-chain supports downstream peptide assembly workflows that require minimized side reactions from the serine hydroxyl.
1. Boc-Based Peptide Building Blocks
Boc-O-methyl-L-Serinedicyclohexylamine salt is used by custom peptide synthesis groups and medicinal chemistry teams to prepare peptide segments containing a serine residue whose side-chain hydroxyl is masked as an O-methyl ether. The Boc protection at the amino terminus supports stepwise peptide assembly strategies, while the O-methyl group helps reduce undesired side reactions associated with free hydroxyl chemistry during chain elongation. This makes the material particularly relevant for constructing protected peptide intermediates and for building libraries where serine positions must remain chemically controlled until the planned deprotection stage.
2. Protected Serine Residue Control
Boc-O-methyl-L-Serinedicyclohexylamine salt supports workflows that require precise control over serine functionality in complex sequences, including peptides with multiple reactive groups or sequences prone to side reactions. By keeping the serine side-chain hydroxyl in an ether-protected state, the building block helps maintain consistency in coupling outcomes and intermediate stability across multistep syntheses. Researchers developing peptide analogs for structure-activity relationship studies often select this type of protected serine derivative to manage orthogonality and to defer hydroxyl reactivity until later processing of the final peptide.
3. Pharmaceutical Intermediate Synthesis
Boc-O-methyl-L-Serinedicyclohexylamine salt is commonly used in pharmaceutical intermediate development where protected amino acid derivatives are required for scalable, reproducible preparation of peptide-based intermediates. The dicyclohexylamine salt form is leveraged in industrial and process chemistry settings to improve the practical handling of the protected amino acid during feeding, weighing, and coupling operations. This product format aligns with downstream manufacturing of protected peptide fragments used in larger synthetic routes, including the preparation of bioactive peptide candidates and their synthetic precursors.
4. Solid-Phase Peptide Segment Preparation
Boc-O-methyl-L-Serinedicyclohexylamine salt is employed in solid-phase peptide synthesis workflows when a protected serine residue is needed within a growing chain and the side-chain hydroxyl must remain masked during assembly. The Boc-protected nature of the amino terminus and the O-methyl side-chain protection support the creation of well-defined peptide segments that can be further processed after cleavage and purification. Peptide chemistry laboratories use this building block to standardize serine incorporation across analog series, where consistent protection patterns are important for reliable downstream deprotection and final peptide characterization.
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