Boc-Cit-OH is a Boc-protected derivative of citrulline, an amino acid featuring a ureido-containing side chain that corresponds to the citrulline backbone while replacing the free α-amino group with a tert-butoxycarbonyl (Boc) protecting group. The molecule therefore bears a carboxylic acid functional group and a ureido side chain capable of hydrogen bonding, with the Boc carbamate masking the α-amino functionality to control chemoselectivity during peptide coupling. Boc-Cit-OH is used as a protected amino acid building block for stepwise peptide synthesis and for preparing citrulline-containing peptide or amino acid derivatives where selective reaction at the carboxyl/activated carboxyl position is required.
CAT No: CP27133
CAS No:45234-13-7
Synonyms/Alias:45234-13-7;Boc-Cit-OH;(S)-2-((tert-Butoxycarbonyl)amino)-5-ureidopentanoicacid;Boc-L-citrulline;Nalpha-Boc-L-citrulline;Boc-L-Cit-OH;Boc-Cit-OH technical;PubChem19004;AC1ODVA4;15474_ALDRICH;SCHEMBL16862524;15474_FLUKA;CTK8C5087;MolPort-003-926-812;ZINC2571888;6237AB;ANW-74035;CB-646;SBB068661;AKOS015836442;AJ-41950;AK-87774;KB-210906;TR-017233;K-9013;(S)-2-((tert-Butoxycarbonyl)amino)-5-ureidopentanoic acid;(2S)-5-(carbamoylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;Boc-Orn(carbamoyl)-OH;Boc-L-Cit-OH;boc-citrulline;Boc-Cit;N5-(Aminocarbonyl)-N2-[(1,1-dimethylethoxy)carbonyl]-L-ornithine;N-(tert-Butoxycarbonyl)citrulline;N-Boc-L-citrulline;Boc-Cit-OH technical;L-Ornithine, N5-(aminocarbonyl)-N2-[(1,1-dimethylethoxy)carbonyl]-;(R)-2-((tert-Butoxycarbonyl)amino)-5-ureidopentanoic acid;SCHEMBL16862524;(S)-2-((tert-Butoxycarbonyl)amino)-5-ureidopentanoicacid;DTXSID20427356;CMJCWQISQGNHHI-ZETCQYMHSA-N;(2S)-2-[(tert-butoxycarbonyl)amino]-5-(carbamoylamino)pentanoic acid;MFCD00080271;(2S)-2-{[(tert-butoxy)carbonyl]amino}-5-(carbamoylamino)pentanoic acid;AKOS015836442;Boc-Cit-OH, technical, >=84% (T);AS-49936;CS-0059158;O10199;EN300-6476848;(S)-2-(tert-butoxycarbonylamino)-5-ureidopentanoic acid
Boc-Cit-OH is a Boc-protected amino acid building block derived from citrulline, supplied in a protected form that is commonly used to control reactivity during peptide assembly. The Boc group on the α-amino functionality supports standard peptide coupling workflows, while the side-chain urea functionality provides a distinct polar motif that is frequently leveraged in peptide and peptidomimetic design. As a protected intermediate, Boc-Cit-OH is typically handled as a synthetic reagent for downstream incorporation into defined peptide sequences rather than as a free amino acid for biochemical assays.
1. Peptide Synthesis Building Block
Boc-Cit-OH is routinely used by peptide synthesis groups to introduce citrulline residues into defined peptide sequences, where the protected α-amino group enables controlled coupling chemistry. Researchers in custom peptide manufacturing and academic peptide chemistry use this reagent for preparing peptides that require the characteristic citrulline side chain, including polar, hydrogen-bonding-rich segments that can influence peptide conformation and solubility. The Boc protection pattern makes it a practical choice for workflows that rely on Boc-compatible protection strategies during stepwise chain assembly.
2. Peptidomimetic And SAR Studies
Boc-Cit-OH supports medicinal chemistry and chemical biology programs that build peptidomimetics or constrained analogs featuring citrulline-like functionality. Medicinal chemistry teams use this building block to generate series of structure-activity relationship (SAR) candidates where the urea-containing side chain is varied in position, context, or neighboring residues to probe how polar side-chain architecture affects target engagement in biochemical assays. Because Boc-Cit-OH is supplied as a protected intermediate, it is well aligned with iterative synthesis of analog libraries and subsequent purification and characterization steps.
3. Defined Urea-Containing Motifs
Boc-Cit-OH is selected when a synthesis plan requires incorporation of a urea-containing, highly polar side chain motif under controlled protection of the amino terminus. Protein and peptide engineering laboratories use citrulline-containing constructs to study sequence-dependent effects such as local charge distribution, hydrogen-bonding networks, and changes in peptide behavior across different solution conditions. By using Boc-Cit-OH as a reagent-level building block, teams can prepare homogeneous, sequence-defined materials suitable for downstream analytical characterization, including LC-MS confirmation of sequence integrity and side-chain presence.
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