Boc-D-Gln-OH is a protected amino acid derivative of D-glutamine, featuring the glutamine side chain with a terminal carboxamide functionality and a free α-amino and α-carboxyl framework masked by an N-protecting group. The N-terminus is protected as a Boc (tert-butoxycarbonyl) carbamate, which controls chemoselectivity by suppressing unprotected amine reactivity while the molecule retains the carboxylic acid for coupling chemistry; the D stereochemical form is indicated by the product name. Boc-D-Gln-OH is used as a building block in peptide synthesis and related amino acid derivatization workflows where stepwise incorporation of a glutamine residue and protection of the amino group are required for controlled assembly and downstream deprotection.
CAT No: CP25938
CAS No:61348-28-5
Synonyms/Alias:Boc-D-Arg(Tos)-OH;61315-61-5;Nalpha-Boc-Nomega-tosyl-D-arginine;N(Alpha)-Boc-N(Omega)-Tosyl-D-Arginine;N-Boc-N'-tosyl-D-arginine;C18H28N4O6S;AmbotzBAA1022;PubChem18954;15184_ALDRICH;15184_FLUKA;CTK3J6912;MolPort-003-926-691;ZINC4534346;ANW-74491;CB-639;KM0490;RTR-021128;AJ-73957;AJ-73958;AK-49979;AN-39363;TR-021128;ST24048775;X5771;J-300026
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-glutamine
Boc-D-Gln-OH is a Boc-protected D-configured glutamine amino acid featuring a side-chain amide that is routinely preserved for downstream coupling and functionalization. The N-terminus is protected as a Boc carbamate, making it a practical building block for peptide assembly workflows that require controlled amine reactivity while maintaining the glutamine side-chain functionality. As a protected amino acid, it is typically handled as a synthetic intermediate for generating defined peptide sequences and related pharmaceutical intermediates rather than as a free amino acid reagent.
1. Solid-Phase Peptide Synthesis
Boc-D-Gln-OH is used by peptide synthesis groups to introduce D-glutamine residues into short peptides and larger peptide constructs during solid-phase peptide synthesis. The Boc protection provides a stable, removable N-terminus that supports selective deprotection and coupling cycles, while the side-chain amide of glutamine remains available for incorporation into the target sequence without converting the side chain into a different functionality. This makes the material particularly useful for researchers building D-amino-acid-containing peptides for sequence control, protease-stability studies, and structure-property investigations where stereochemistry at the amino acid center matters.
2. D-Amino-Acid Peptide Libraries
Boc-D-Gln-OH is commonly selected for peptide library construction and SAR-style analog generation where D-amino-acid substitution is used to probe conformational effects and sequence-dependent behavior. In library workflows, the protected glutamine building block helps maintain consistent side-chain chemistry across variants, enabling systematic comparison of peptides that differ by stereochemistry or sequence context while keeping the glutamine side-chain as an amide. Medicinal chemistry and chemical biology teams often use this type of protected D-amino-acid input to generate defined analog panels for downstream binding, aggregation, or biophysical characterization in a controlled manner.
3. Pharmaceutical Intermediate Building Block
Boc-D-Gln-OH is also used as a pharmaceutical intermediate building block for the preparation of peptide-like fragments, peptidomimetic scaffolds, and protected D-amino-acid segments used in custom synthesis. The combination of Boc N-protection and a glutamine side-chain amide supports stepwise assembly of intermediates that require a stable amino functionality during multi-step processing. Process development and specialty chemical manufacturing teams rely on such protected amino acids to standardize inputs for downstream coupling, fragment condensation, and purification workflows where defined stereochemistry and functional group preservation are critical.
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