N-Me-Ser(tBu)-OH is a protected serine derivative in which the amino group is N-methylated and the side-chain hydroxyl is protected as a tert-butyl ether, retaining the amino acid backbone with a free carboxylic acid. The molecule bears a carboxyl group (-COOH) and a secondary amide-like nitrogen due to N-methylation, while the serine side chain is masked as an O-tert-butyl substituent to modulate polarity and chemoselectivity during synthesis. N-Me-Ser(tBu)-OH is used as a stepwise building block or intermediate for preparing serine-containing peptides and peptide analogues, and the combination of N-methylation with O-tert-butyl protection supports controlled functional group manipulations in peptide chemistry and related derivative synthesis.
CAT No: CP26609
CAS No:197632-83-0
Synonyms/Alias:N-Me-Ser(Tbu)-OH;197632-83-0;SCHEMBL1693987;MolPort-020-004-024;ZINC2389801;AKOS006276873;AJ-35622;AK-88954;4CH-023838;L-Serine,O-(1,1-dimethylethyl)-N-methyl-;ST24048595;Z5710;K-5791;(S)-2-(Methylamino)-3-tert-butoxypropanoicacid;I14-33440;(2S)-2-(methylamino)-3-[(2-methylpropan-2-yl)oxy]propanoicacid
N-Me-Ser(tBu)-OH is a protected serine derivative in which the amino functionality is N-methylated (N-Me) and the hydroxyl side chain is protected as a tert-butyl ether (Ser(tBu)). The molecule retains the stereogenic center characteristic of L-serine while presenting a carboxylic acid handle suitable for conversion into peptide coupling partners or downstream functionalization. The combination of an N-methylated nitrogen and a tert-butyl-protected hydroxyl provides orthogonal protection behavior that can be selectively removed under controlled conditions, enabling stepwise assembly of protected amino acid building blocks. The presence of a free carboxylic acid and a protected alcohol also supports predictable reactivity patterns typical of amino acid esterification, amide formation, and controlled deprotection chemistry in peptide and synthetic organic workflows.
1. Peptide Synthesis
N-Me-Ser(tBu)-OH supports peptide coupling workflows by providing a serine-based residue with a protected side-chain alcohol, allowing amide bond formation through its carboxylic acid while minimizing side reactions from the unprotected hydroxyl group. The N-methylation alters the amide nitrogen reactivity and can be used to tune peptide backbone properties in peptidomimetic designs, including reduced hydrogen-bonding capacity at that position. tert-Butyl protection of the side-chain oxygen enables selective deprotection after chain assembly to generate a free serine hydroxyl for subsequent phosphorylation, glycosylation, or crosslinking strategies. The stereodefined serine center helps maintain consistent stereochemistry during peptide construction and analog generation for structure-focused studies.
2. Peptidomimetics And SAR
N-Me-Ser(tBu)-OH is suitable for peptidomimetic and structure-activity relationship studies where an N-methylated serine residue is used to modulate conformational preferences and backbone polarity. The protected hydroxyl (tBu ether) preserves the serine side chain during iterative synthesis, supporting late-stage functionalization once the molecular scaffold is assembled. The carboxylic acid enables incorporation into amide-linked analogs and fragment coupling strategies that maintain defined stereochemistry at the serine chiral center. Downstream deprotection can reveal a reactive serine alcohol for generating SAR libraries through hydroxyl derivatization, enabling systematic evaluation of side-chain chemistry effects in medicinal chemistry contexts.
3. Amino Acid Derivatization
N-Me-Ser(tBu)-OH functions as a chiral amino acid intermediate for side-chain functionalization chemistry, leveraging the protected serine hydroxyl to control timing of reactivity. tert-Butyl protection reduces undesired alcohol participation during carboxyl activation and amide formation, while the N-methyl group provides a distinct nitrogen environment for subsequent transformations or for preparing N-methylated peptide fragments. The free carboxylic acid can be converted into activated derivatives for coupling to amines or for building ester-linked intermediates, supporting synthetic routes that require controlled functional group presentation. Resulting derivatives can serve as intermediates for hydroxyl-containing bioactive analogs, polymerizable monomers, or chemical probes derived from serine chemistry.
4. Chemical Biology Probes
N-Me-Ser(tBu)-OH can be applied in chemical biology research to generate serine-containing probes and tagged fragments where orthogonal protection supports stepwise conjugation. The N-methylated backbone position can be used to tune probe stability and reduce amide exchange or hydrogen-bond-driven aggregation during labeling workflows. The protected side-chain hydroxyl enables compatibility with multi-step synthesis, with later deprotection providing a handle for conjugation chemistries that require a free alcohol functionality. The stereochemically defined serine center supports consistent molecular recognition in probe design, facilitating downstream assembly of labeled peptides, peptide mimics, or small-molecule reporters.
5. Pharmaceutical Intermediate Preparation
N-Me-Ser(tBu)-OH is relevant to pharmaceutical intermediate preparation where protected amino acid fragments are manufactured for incorporation into peptide-like scaffolds and hydroxyl-bearing intermediates. The tert-butyl ether protection strategy supports manufacturing route design by suppressing side-chain reactivity during activation of the carboxylic acid and coupling to amine partners. The N-methylated amide character can be exploited to prepare N-methylated peptide building blocks that align with downstream synthetic requirements for backbone-modified candidates. The resulting protected amino acid intermediate can be carried through controlled deprotection steps to furnish serine hydroxyl functionality for subsequent derivatization in fine chemical synthesis and applied process chemistry.
6. Process Chemistry Intermediate
N-Me-Ser(tBu)-OH serves as a chiral process chemistry intermediate for scalable synthesis of protected serine derivatives used in peptide coupling and downstream functional group installation. The orthogonal protection pattern, combining an N-methylated nitrogen with a tert-butyl-protected alcohol, supports sequential transformations where carboxyl activation and controlled deprotection can be orchestrated to minimize impurity formation from reactive side-chain groups. The stereogenic serine core provides a defined chiral building block for producing consistent intermediate profiles across synthetic batches. The compound's functional group layout enables conversion into coupling-ready forms and subsequent derivatization into hydroxyl-functional products used in industrial fine chemical production and peptide-scaffold manufacturing.
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