D-Homoserine is a non-proteinogenic amino acid featuring a three-carbon (propyl) side chain terminating in a primary alcohol, distinguishing it from the shorter side chain of threonine and from the carboxyl-bearing side chain of aspartate. The molecule contains a free amino group and a free carboxyl group along with a hydroxyl functional group on the side chain, and the "D-" designation indicates the D stereochemical form at the α-carbon. As a chemically defined amino acid building block, D-Homoserine is used in peptide and amino acid derivative synthesis and in structure-activity or labeling studies where the hydroxymethyl side chain provides a handle for further functionalization or conjugation.
CAT No: CP06603
D-Homoserine is a chiral aliphatic amino acid featuring a stereogenic center at the alpha carbon and an extended side chain terminating in a primary hydroxyl group, enabling both hydrogen-bonding interactions and selective functional group transformations. The molecule contains a free amino functionality and a carboxylic acid, which together support salt formation, acid-base tuning, and predictable reactivity in peptide coupling and derivatization chemistry. The hydroxyl-bearing side chain can be protected as an ether or ester to control chemoselectivity during N- or C-terminal modifications. As an amino acid intermediate, D-homoserine participates in stereochemically defined syntheses where retention of configuration and controlled protection/deprotection strategies govern downstream product profiles.
1. Protected Amino Acid Chemistry
D-Homoserine supports protected amino acid synthesis workflows where orthogonal protection of the amino and hydroxyl groups enables stepwise C-terminal activation and N-protection without side-chain interference. The primary alcohol can be converted to an ether or ester protecting group to suppress undesired esterification or transesterification during coupling chemistry, while the carboxylic acid can be maintained for activation to amide-forming intermediates. The D-configuration at the alpha stereocenter provides chiral integrity for producing stereodefined protected derivatives used as peptide building blocks. Downstream, protected D-homoserine derivatives can be employed in fine chemical synthesis and process chemistry intermediate preparation for amino acid ester and amide intermediates.
2. Peptide Synthesis
D-Homoserine is suitable for peptide construction strategies that incorporate a hydroxyl-functional side chain for subsequent post-coupling modification or for direct inclusion in peptide scaffolds. The amino and carboxyl functionalities enable standard peptide coupling logic after appropriate activation of the acid and protection of the amine, while side-chain hydroxyl protection supports chemoselective amide bond formation. D-homoserine-derived residues can be used to generate peptides that present a stereodefined, hydrogen-bonding side chain for controlling conformation and intermolecular recognition. Resulting peptide intermediates and analogs can be used in biochemical research intermediate preparation, SAR studies, and peptidomimetic construction where side-chain functional groups are retained for later derivatization.
3. Side-Chain Functionalization
D-Homoserine enables side-chain functionalization chemistry through its primary hydroxyl group, which can be transformed into leaving groups, protected alcohol derivatives, or functional handles for further synthetic elaboration. The presence of a chiral amino acid backbone allows stereochemically consistent conversion of the side chain while maintaining the D-configuration for downstream stereoselective steps. Hydroxyl derivatization can support formation of O-alkyl or O-acyl derivatives, enabling incorporation into larger molecular frameworks such as heterocycle precursors or conjugation-ready intermediates. The resulting functionalized amino acid derivatives can serve as intermediates for specialty chemical production and applied synthesis of chiral building blocks used in industrial fine chemical manufacturing.
4. Chiral Building Block Development
D-Homoserine functions as a chiral amino acid intermediate for developing D-configured building blocks used in stereocontrolled synthesis of amino acid derivatives and related chiral frameworks. The alpha-amino acid stereocenter provides a defined stereochemical element that can be carried through protecting-group strategies, including selective N-protection and hydroxyl protection to manage reactivity during multi-step sequences. Side-chain hydroxyl functionality offers a handle for converting to protected forms that can survive activation chemistry and later be revealed for targeted transformations. Chiral derivatives derived from D-homoserine can be employed in process chemistry intermediate preparation and in the synthesis of stereochemically defined compounds for research and industrial manufacturing routes.
5. Bioconjugation And Chemical Biology
D-Homoserine can be applied in chemical biology and bioconjugation contexts where amino acid-derived linkers or functionalized side chains provide controlled attachment chemistry. The hydroxyl-bearing side chain supports derivatization into conjugation-ready motifs, while the amino acid backbone can be protected and activated to generate amide-forming or coupling-capable intermediates compatible with biomolecule labeling strategies. D-configuration can be leveraged when stereochemical identity of the linker or residue influences binding orientation or enzymatic processing in biochemical assays. Downstream, D-homoserine-derived conjugation intermediates can be used for generating labeled peptides, linker-functionalized probes, and analytical standards that support structure-function studies in amino acid chemistry and peptide science.
6. Pharmaceutical Intermediate Preparation
D-Homoserine is relevant to pharmaceutical intermediate preparation and industrial fine chemical synthesis due to its straightforward conversion into protected amino acid derivatives, activated esters, and amide-forming intermediates. The combination of a carboxylic acid and a primary alcohol supports manufacturing route design that uses orthogonal protection to enable selective transformations while minimizing side reactions. D-homoserine-derived intermediates can be incorporated into larger synthetic sequences to construct stereodefined fragments bearing hydroxyl functionality, which can be carried forward for further functional group interconversions. The resulting amino acid-based intermediates can serve as process chemistry inputs for specialty chemical production where controlled stereochemistry and functional group compatibility are required.
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