Boc-Ile-Gly-OH is a Boc-protected dipeptide building block composed of isoleucine and glycine, where the N-terminus is capped with a tert-butoxycarbonyl (Boc) protecting group and the molecule retains a free C-terminal carboxylic acid. The amino acid residues present an isoleucine side chain with a branched aliphatic functionality and a glycine side chain of hydrogen, while the peptide backbone contains the characteristic amide linkages between residues and the terminal amino functionality is masked by the Boc group. This protected peptide intermediate is used in peptide synthesis workflows to control chemoselectivity at the N-terminus and to enable stepwise assembly of longer peptide structures in solution-phase or solid-phase strategies.
CAT No: CP26451
CAS No:16257-05-9
Synonyms/Alias:BOC-ILE-GLY-OH;16257-05-9;ZINC2522582;AKOS022181241;AJ-37208;AK-60631;N-[N-(tert-Butoxycarbonyl)-L-isoleucyl]glycine;2-((2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-methylpentanamido)aceticacid
Boc-Ile-Gly-OH is a Boc-protected dipeptide building block featuring an isoleucine residue linked to glycine, supplied as the carboxylic acid for downstream peptide assembly. The N-terminal Boc group supports controlled coupling in peptide synthesis workflows, while the free carboxylate enables further elongation or conversion to activated derivatives. This structure is frequently used by peptide chemistry groups to prepare defined peptide segments with minimal ambiguity in chain length and protecting-group pattern.
1. Segment Coupling In Peptides
Boc-Ile-Gly-OH is used as a protected dipeptide segment for stepwise peptide synthesis, particularly when researchers need a defined Ile-Gly motif as part of a longer chain. Peptide synthesis teams in academic and industrial settings rely on this format to streamline fragment condensation, where the Boc-protected N-terminus provides compatibility with standard peptide coupling strategies and helps maintain the intended sequence during assembly. The presence of a free C-terminal carboxylic acid supports subsequent activation for coupling to the next residue, enabling controlled growth of peptide targets such as peptide libraries, sequence-optimized analogs, and reference fragments used in structure-activity studies.
2. Solution-Phase And Automated Assembly
Boc-Ile-Gly-OH is frequently selected for solution-phase peptide synthesis and for workflows that use preformed peptide fragments rather than building every residue from single amino acids. In custom peptide manufacturing and research laboratories, the dipeptide format reduces the number of coupling steps required to introduce the Ile-Gly unit, which can improve throughput when assembling multiple analogs. The Boc-protected N-terminus and the C-terminal acid functionality make the material practical for integration into iterative elongation schemes, including preparation of intermediate peptides for later purification and downstream functionalization.
3. Peptide Library And SAR Intermediates
Boc-Ile-Gly-OH serves as a practical intermediate for generating peptide libraries and SAR (structure-activity relationship) series where Ile-Gly is a recurring sequence element. Medicinal chemistry groups and peptide discovery teams often incorporate such defined dipeptide blocks to rapidly produce analog panels with consistent stereochemical and sequence fidelity. By using a preassembled Ile-Gly fragment, developers can focus optimization efforts on the surrounding residues and functional modifications, while maintaining tight control over the specific backbone segment that influences conformation, proteolytic processing behavior in assay systems, or binding-site geometry in biochemical evaluations.
4. Defined Standards For Analytical Method Development
Boc-Ile-Gly-OH is also used as a defined peptide reference material during analytical method development and characterization of peptide synthesis workflows. Analytical chemistry teams preparing LC-MS methods, HPLC purification scouting, or MS/MS acquisition parameters benefit from having an unambiguous, sequence-defined dipeptide acid with a known protecting-group pattern at the N-terminus. This enables consistent monitoring of coupling outcomes, assessment of intermediate identity, and verification of fragment incorporation during process development for peptide intermediates and final peptide products.
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