Boc-Pro-Gly-OH is a Boc-protected dipeptide acid composed of proline and glycine, where the N-terminus is carbamate-protected by a tert-butoxycarbonyl (Boc) group and the C-terminus is present as a free carboxylic acid. The molecule contains a proline ring side chain and a glycine residue, with an amide linkage between the two amino acid units and a Boc-protected amino functionality that suppresses undesired amine reactivity during handling and coupling. Boc-Pro-Gly-OH is used as a peptide-building intermediate in stepwise peptide synthesis and related derivatization workflows, including the controlled assembly of peptide fragments where N-protection supports chemoselective formation of subsequent peptide bonds.
CAT No: CP27164
CAS No:51785-82-1
Synonyms/Alias:BOC-PRO-GLY-OH;51785-82-1;SCHEMBL3591879;CTK8F8309;PLJXCLBLFPFXEN-QMMMGPOBSA-N;ZINC2560857;N-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-ylcarbonyl]glycine
Boc-Pro-Gly-OH is a Boc-protected proline-glycine amino acid derivative designed for peptide and peptidomimetic assembly workflows where a protected N-terminus is required for controlled coupling. The proline ring provides a conformationally constrained secondary amine side chain, while the glycine residue contributes a minimal side chain for backbone flexibility. As a Boc-protected building block, it is commonly handled as a stable, isolable intermediate for stepwise synthesis of peptides and for preparing defined segments with an N-protected amino functionality.
1. Peptide Segment Coupling
Boc-Pro-Gly-OH is used by peptide synthesis groups to build defined Pro-Gly segments in solution-phase or automated peptide assembly workflows, particularly when a Boc-protected N-terminus is advantageous for sequential bond formation. Researchers selecting this derivative often need a reliable, isolable intermediate that carries the N-protection required to prevent premature reactivity during coupling steps. The Pro-Gly sequence is frequently incorporated into peptide libraries and structure-activity relationship studies where conformational effects from proline and backbone flexibility from glycine are both relevant to downstream peptide behavior.
2. Protected Dipeptide Intermediate
Boc-Pro-Gly-OH serves as a protected dipeptide intermediate for pharmaceutical intermediate development and custom peptide manufacturing, where consistent segment quality and controlled functional group availability are critical. Process and R&D teams typically use such Boc-protected building blocks to standardize the introduction of a Pro-Gly motif into longer peptide chains, reducing variability associated with in situ generation of reactive fragments. The product's protected amino functionality supports stepwise assembly strategies that require temporary protection of the N-terminus while the growing peptide undergoes further coupling and purification.
3. Peptidomimetic And Library Synthesis
Boc-Pro-Gly-OH is also applied in peptidomimetic and peptide library synthesis to generate Pro-Gly-containing analogs for chemical biology and medicinal chemistry research programs. Teams developing constrained or backbone-modified peptide analogs often favor proline-containing motifs to influence local conformations, while glycine helps maintain flexibility at specific positions. By using a Boc-protected dipeptide building block, researchers can incorporate the Pro-Gly unit as a discrete, well-defined fragment, enabling parallel synthesis of multiple analogs with consistent sequence composition for downstream characterization and SAR workflows.
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