N-Me-cis-Hyp-OH is an N-methylated, cis-configured hydroxyproline derivative in which the pyrrolidine ring bears a side-chain hydroxyl group characteristic of Hyp and a carboxylic acid for amino acid functionality. The molecule contains an N-methylated amine (tertiary amide-like substitution pattern at the nitrogen) and a free carboxyl group, with the "cis" descriptor indicating the relative stereochemical arrangement of substituents on the ring. As a structurally modified hydroxyproline building block, it is used in peptide and peptidomimetic synthesis and structure-activity or conformational studies where N-methylation and cis stereochemistry are used to tune backbone geometry and hydrogen-bonding behavior.
CAT No: CP27352
CAS No:67463-44-9
Synonyms/Alias:67463-44-9;(2S,4S)-4-Hydroxy-1-methylpyrrolidine-2-carboxylicacid;N-Me-cis-Hyp-OH;N-Methyl-L-allohydroxyproline;SCHEMBL689733;N-ME-CIS-HYDROXYPROLINE;CTK2F2384;MolPort-035-757-716;N-Methyl-cis-4-hydroxy-L-proline;1-Methyl-cis-4-hydroxy-L-proline;ZINC33995324;(4S)-4-Hydroxy-1-methyl-L-proline;AKOS006276573;AK162678;L-Proline,4-hydroxy-1-methyl-,(4S)-;FT-0698801
N-Me-cis-Hyp-OH is a chiral, amino-acid-derived building block featuring a N-methylated imino acid framework consistent with cis-4-hydroxyproline (cis-Hyp) stereochemistry and a free carboxylic acid for downstream coupling. The molecule contains a hydroxyl-bearing side chain that can participate in hydrogen bonding and selective derivatization, while the N-methyl substitution modulates amide formation reactivity and conformational preferences in peptide contexts. The stereodefined cis relationship at the proline ring and the presence of an unprotected carboxyl group make it suitable for controlled peptide bond formation and for constructing constrained peptidomimetic scaffolds. The hydroxyl functionality can be protected or transformed to enable selective side-chain chemistry, supporting both stereochemically consistent synthesis and later functional group interconversions.
1. Peptide Synthesis
N-Me-cis-Hyp-OH is applied in peptide coupling workflows where a stereodefined N-methylated proline residue is required to build conformationally constrained sequences. The free carboxylic acid enables activation for amide bond formation, while the N-methylated nitrogen and cis-4-hydroxy stereochemistry help preserve backbone geometry during peptide assembly. The side-chain hydroxyl can be protected during coupling and later deprotected or derivatized to generate hydroxyl-bearing peptide analogs or further functionalized residues. Incorporation of N-methyl cis-hydroxyproline into peptide building blocks can support the synthesis of cyclic or turn-stabilized peptides used in structure-function studies and peptide chemistry development.
2. Peptidomimetics And SAR
N-Me-cis-Hyp-OH is used in peptidomimetic construction and structure-activity relationship studies where proline-like rigidity and hydroxyl-mediated interactions are leveraged to tune molecular recognition. The N-methyl group restricts amide conformations and can influence hydrogen-bonding patterns relative to non-methylated analogs, while the cis stereochemistry provides a defined ring orientation. The side-chain hydroxyl supports derivatization strategies such as esterification, ether formation, or conversion to leaving groups for subsequent scaffold elaboration. Downstream analog generation from this chiral amino acid intermediate can feed medicinal chemistry campaigns focused on mapping how stereochemistry and functional group placement affect binding profiles.
3. Chemical Biology Labels
N-Me-cis-Hyp-OH supports chemical biology research requiring incorporation of a defined chiral hydroxyproline motif into labeled peptides or biomolecule-reactive probes. The hydroxyl group enables controlled functionalization into activated handles for conjugation chemistry, while the carboxyl functionality allows attachment to coupling partners through amide formation or activation to form stable linkages. The N-methylated cis proline framework can be used to generate constrained peptide conjugates that maintain structural fidelity during labeling and subsequent analytical readouts. The resulting labeled or derivatized constructs can serve as reagents for probing recognition events, monitoring peptide processing, or creating standardized materials for biochemical assays.
4. Protected Amino Acid Derivatives
N-Me-cis-Hyp-OH is suitable for preparing protected amino acid derivatives used in protected amino acid synthesis and stepwise peptide building block preparation. The free carboxylic acid can be converted into activated or protected forms compatible with orthogonal deprotection schemes, while the side-chain hydroxyl can be selectively protected to prevent undesired reactions during coupling. The N-methylated nitrogen generally remains non-protected in many coupling strategies, simplifying handling while still providing the stereochemically defined proline core. Conversion to downstream protected intermediates can support scalable fine chemical synthesis routes for manufacturing peptide fragments and chiral intermediates.
5. Process Chemistry Intermediate
N-Me-cis-Hyp-OH is employed as a chiral amino acid intermediate in process chemistry where stereochemical integrity and functional group management are central to reliable manufacturing. The combination of a free carboxylic acid and a hydroxyl side chain enables design of robust activation, protection, and conversion sequences that align with industrial amino acid derivatization practices. The cis-4-hydroxyproline stereochemistry and N-methyl substitution provide a defined chiral scaffold for producing consistent peptide building blocks and peptidomimetic intermediates. Downstream formation of protected or activated derivatives from this material can support specialty chemical production and pharmaceutical intermediate preparation workflows that require reproducible stereochemical outcomes.
6. Analytical Research Standards
N-Me-cis-Hyp-OH can be used to generate analytical research standards and reference materials for method development in amino acid and peptide analysis. The defined stereochemistry, N-methyl substitution, and hydroxyl functionality provide a discriminating signature for chromatographic separation and mass spectrometric characterization of proline-derived motifs. The compound's carboxylic acid and hydroxyl group enable derivatization strategies for analytical workflows, including formation of detectable derivatives or incorporation into peptide standards. Reference-grade use of this chiral amino acid building block can support quality control of peptide synthesis, characterization of hydroxyproline-containing fragments, and verification of stereochemical integrity in synthetic chemistry programs.
1. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
2. High fat diet and GLP-1 drugs induce pancreatic injury in mice
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