D-Isoserine is the D-stereoisomer of the proteinogenic amino acid isoserine, featuring an α-amino and α-carboxyl functional group attached to a side chain bearing a hydroxymethyl substituent. The amino acid exists as a zwitterionic species in typical aqueous conditions and, as a stereochemically defined D-form, can be used to control stereochemical outcomes in peptide and small-molecule synthesis where stereochemistry matters. D-Isoserine is employed in amino acid derivative preparation, stereochemical structure-activity studies, and analytical or labeling workflows that require a defined non-L amino acid building block for incorporation into peptide-like structures or for comparative studies of amino acid behavior.
CAT No: CP07703
D-Isoserine is the D-enantiomer of the proteinogenic amino acid isoserine, featuring a chiral α-carbon bearing a primary amino group and a side-chain hydroxymethyl functionality (CH2OH) attached to the carbon skeleton. The molecule's stereochemistry determines its behavior in asymmetric synthesis, enzymatic recognition, and derivatization selectivity, while the free amino and alcohol groups provide complementary nucleophilic and hydrogen-bonding sites for chemical modification. D-Isoserine can be converted into protected amino acid derivatives or activated intermediates for incorporation into larger structures, and its hydroxyl group can participate in esterification, ether formation, or oxidation to carbonyl-containing analogs. The presence of both amine and alcohol functionality makes D-isoserine a practical chiral building block for amino acid derivatization and for downstream synthesis of stereodefined intermediates used in peptide and heterocycle chemistry.
1. Chiral Building Block
D-Isoserine supports chiral synthesis programs in asymmetric organic chemistry and fine chemical development by providing a stereodefined amino alcohol framework. The D-configuration at the α-carbon, combined with the side-chain CH2OH group, enables stereocontrolled derivatization such as selective protection of the amine and conversion of the hydroxymethyl group into an ester, carbonate, or ether. The resulting protected or functionalized derivatives can serve as chiral amino acid intermediates for preparing downstream stereodefined compounds, including N-alkylated or N-acylated analogs and oxygen-functionalized chiral fragments. D-Isoserine thus functions as a practical input for building stereochemically encoded molecules where amino alcohol recognition and hydrogen-bonding patterns matter in synthesis planning.
2. Protected Amino Acid Synthesis
D-Isoserine is suitable for protected amino acid chemistry workflows where controlled reactivity of the amine and alcohol groups is required during multi-step synthesis. The amino group can be masked using standard N-protecting groups, while the side-chain hydroxyl can be protected as an ester or carbonate to prevent undesired participation in coupling or activation steps. The stereochemically defined D-amino acid derivative can then be activated for peptide coupling chemistry or used to prepare C-terminal and side-chain modified intermediates under orthogonal protection strategies. Downstream, these protected forms enable systematic exploration of amino acid derivatization patterns and support the production of stereodefined building blocks for peptide-like structures and synthetic intermediates.
3. Peptide Coupling Chemistry
D-Isoserine can be applied in peptide synthesis planning as a D-amino acid component for constructing stereochemically defined peptide sequences and peptidomimetic scaffolds. The presence of a primary amino functionality and a hydroxymethyl side chain allows conversion into activated coupling partners or protected peptide building blocks compatible with standard amide bond formation strategies. The D-configuration enables incorporation of D-isoserine residues into peptide analogs to modulate backbone stereochemistry, side-chain polarity, and hydrogen-bonding networks relative to L-isomer counterparts. The hydroxymethyl group can further be functionalized after coupling to generate side-chain variants, supporting iterative structure-activity relationship studies in peptide science and biochemical research intermediate preparation.
4. Chemical Biology Probes
D-Isoserine is relevant to chemical biology research as a chiral amino acid handle for designing probes and labeled analogs that rely on amino alcohol functionality. The amino group can be derivatized for attachment to linkers, affinity tags, or reporter moieties, while the side-chain hydroxymethyl group can be transformed into reactive intermediates for conjugation chemistry. Stereochemical fidelity of the D-enantiomer can be leveraged to tune binding selectivity in recognition processes where stereochemistry governs molecular interactions. The resulting labeled or functionalized D-isoserine derivatives can serve as biochemical research intermediates for studying substrate preferences, transport processes, or enzyme-compatible recognition motifs in vitro.
5. Heterocycle And Functional Intermediate
D-Isoserine can be employed in synthetic organic chemistry for heterocycle construction and for generating functional chiral intermediates from an amino alcohol precursor. The side-chain hydroxymethyl group and the amino functionality enable conversion into cyclic or oxygenated motifs through dehydration, oxidation-reduction sequences, or intramolecular cyclization strategies after appropriate protection and activation. The D-stereocenter can be retained through carefully designed transformations, supporting access to stereodefined heterocyclic building blocks and oxygen-containing chiral fragments. Downstream use includes preparation of chiral intermediates for pharmaceutical intermediate development, specialty chemical production, and process chemistry routes where robust functional group interconversion from an amino alcohol starting point is required.
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