CAT No: CP25245
CAS No:124605-42-1
Synonyms/Alias:124605-42-1;(2R,3S)-N-Boc-3-phenylisoserinemethylester;Methyl(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate;(2R,3S)-2-hydroxy-3-(N-tertbutoxycarbonyl)amino-3-phenyl-methylpropionate;Methyl(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate;(2R,3S)-N-tert-butoxycarbonyl-3-phenyl-isoserinemethylester;SCHEMBL6784979;Jsp006071;CTK4B4007;MolPort-003-984-010;NCALQERIBRYGOK-NWDGAFQWSA-N;Benzenepropanoicacid,b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxy-,methylester,(aR,bS)-;AC-517;ANW-46099;ZINC12506667;AKOS015964432;AJ-62610;AK-41309;AN-15793;H675;KB-53568;AB0009940;TC-134844;FT-0657490;ST24026163
Chemical Name:(2R,3S)-N-t-Butoxycarbonyl-3-phenylisoserine methyl ester, (2R,3S)-2-Hydroxy-3-(N-t-butyloxycarbonyl)amino-3-phenylmethyl propionate, ee >99%
Boc-RS-iSer(3-Ph)-OMe is a Boc-protected serine derivative bearing an O-methyl ester and a phenyl-substituted side-chain at the iSer position, provided in a racemic (RS) form. This protected amino acid building block is designed for peptide and peptidomimetic assembly where controlled stereochemistry at the serine-derived center is not required, while the Boc group and ester functionality support downstream coupling and segment construction. The phenyl substituent increases hydrophobic character and provides a handle for SAR-focused medicinal chemistry and conformational effects in synthetic peptides.
1. Peptidomimetic Building Block
Boc-RS-iSer(3-Ph)-OMe is used as a non-natural amino acid building block for constructing peptidomimetics and modified peptide analogs in medicinal chemistry programs. Researchers incorporate this serine-derived residue to introduce a phenyl-bearing side-chain that can modulate local hydrophobicity and steric environment, supporting structure-activity relationship (SAR) studies. The Boc protection on the amino terminus and the methyl ester on the carboxyl side enable it to function as a defined synthetic segment in custom peptide synthesis workflows, including library generation where rapid iteration of residue identity is required.
2. Solid-Phase Peptide Synthesis
Boc-RS-iSer(3-Ph)-OMe is commonly selected for solid-phase peptide synthesis (SPPS) workflows when a protected, pre-defined residue is needed for stepwise chain assembly. Peptide synthesis teams use Boc-protected amino acid derivatives to streamline coupling of modified residues into peptide sequences, particularly when the target sequence contains non-standard side-chain features such as a phenyl-substituted iSer motif. The O-methyl ester provides a controlled carboxyl functionality during segment handling, supporting the preparation of peptide intermediates and sequence variants intended for subsequent conversion to the corresponding free acid or for further downstream modifications depending on the synthetic plan.
3. Pharmaceutical Intermediate Development
Boc-RS-iSer(3-Ph)-OMe serves as a practical pharmaceutical intermediate for preparing higher-complexity amino acid derivatives and peptide-like intermediates used in development chemistry. Process and synthetic development groups use such Boc-protected, functionalized amino acid building blocks to access defined stereochemical variants, side-chain-modified fragments, and protected intermediates that can be carried into subsequent coupling, derivatization, or purification steps. The phenyl-substituted side chain makes this residue particularly useful when developers need a hydrophobic substituent embedded within an amino acid framework to support optimization of chemical properties in lead series.
4. SAR Peptide Library Synthesis
Boc-RS-iSer(3-Ph)-OMe is frequently employed in SAR-focused peptide library synthesis where rapid comparison of residue-level modifications is required. Chemical biology and medicinal chemistry groups use this building block to generate analog sets that differ by a single side-chain feature, enabling systematic evaluation of how phenyl substitution at the serine-derived position influences peptide conformation and physicochemical behavior. The racemic (RS) supply is advantageous for exploratory library stages where the primary goal is to establish structure-property trends before committing to stereodefined optimization, while the Boc/ester protection pattern supports consistent incorporation into peptide sequences during parallel synthesis.
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