Boc-D-Homocitrulline is a protected, D-configured amino acid derivative featuring an N-terminal Boc (tert-butoxycarbonyl) carbamate on the amino group and a carboxylic acid functionality, with a side chain related to citrulline that bears an additional methylene unit (homocitrulline). The molecule contains the Boc-protected α-amino group and the free carboxyl group, while the side-chain urea functionality provides a polar, hydrogen-bonding capable motif that can participate in substrate-reagent interactions during peptide assembly or derivatization. In peptide chemistry, Boc-protected amino acids such as this one are used as stepwise building blocks in protected amino acid strategies, supporting controlled chemoselectivity at the α-amino position while the side-chain functionality can be carried through synthesis or used for subsequent structure-activity and labeling studies.
CAT No: CP06205
CAS No:121080-97-5
Synonyms/Alias:121080-97-5;Boc-D-homocitrulline;(R)-2-((tert-Butoxycarbonyl)amino)-6-ureidohexanoicacid;BOC-D-HCIT-OH;CTK8B8538;MolPort-020-003-804;ZINC2517134;ANW-60633;AKOS015911616;AJ-37032;AK-87796;KB-209692;RT-021668;K-1504;I14-37333
Boc-D-Homocitrulline is a D-configured homocitrulline amino acid building block bearing a Boc-protecting group on the alpha-amino functionality, making it a protected amino acid suited to controlled peptide assembly. Its side chain contains the characteristic urea/guanidino-like functionality of homocitrulline derivatives, which is frequently leveraged to introduce strongly hydrogen-bonding and charge-delocalized motifs into peptides and peptidomimetics. As a stereochemically defined, protected intermediate, it is commonly selected when downstream coupling requires an amino-protected form that can be incorporated into peptide segments without premature side-chain reactivity.
1. Protected Segment Building Block
Boc-D-Homocitrulline is used as a protected amino acid segment for peptide synthesis workflows where a D-stereocenter and homocitrulline-derived side chain are required to control stereochemistry and local interaction patterns. Peptide synthesis teams in academic and industrial settings incorporate it into solution-phase or custom peptide assembly strategies to generate peptides and peptidomimetics that contain urea/guanidino-like hydrogen-bonding motifs. The Boc protection on the alpha-amino group supports stepwise coupling and purification between synthetic steps, while the D-configuration enables stereochemical tuning in structure-activity relationship (SAR) studies and conformational investigations.
2. Peptidomimetic And Analog Development
Boc-D-Homocitrulline is frequently selected for the preparation of peptidomimetic analogs that emulate key interaction features associated with homocitrulline-containing motifs in bioactive peptide scaffolds. Medicinal chemistry groups use this building block to introduce a D-homocitrulline residue into constrained or modified peptide frameworks, supporting systematic variation of stereochemistry and side-chain presentation. In this role, the protected alpha-amino functionality helps maintain synthetic control during fragment condensation, while the homocitrulline side chain provides a strong pattern of hydrogen-bonding and charge-delocalization that is valuable for mapping binding interactions and optimizing peptide-like ligands.
3. Stereochemical SAR Probing
Boc-D-Homocitrulline supports stereochemical probing in SAR campaigns where D-amino acid incorporation is used to evaluate how stereochemistry influences peptide conformation, recognition, and structure-property relationships. Research groups preparing libraries of D-configured peptide analogs rely on this Boc-protected intermediate to ensure consistent coupling behavior and reproducible residue placement within multi-residue sequences. The combination of D-configuration and a protected alpha-amino group makes it a practical choice for generating matched series of analogs that differ primarily at stereochemical or sequence-defined positions, enabling clearer interpretation of structure-activity trends.
4. Pharmaceutical Intermediate Synthesis
Boc-D-Homocitrulline is also used as a defined protected intermediate in the development of advanced peptide-derived chemical entities and related synthetic intermediates for pharmaceutical research. Process development and custom manufacturing teams employ this building block to assemble protected peptide fragments or to route homocitrulline-containing motifs into larger synthetic sequences under controlled conditions. The Boc-protected alpha-amino group and the stereodefined D-center help standardize intermediate quality for downstream transformations, making it useful for producing consistent material for further derivatization, purification, and analytical characterization within medicinal chemistry and CMC-adjacent workflows.
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