Boc-D-NptGly-OH is a protected amino acid derivative in which glycine is substituted with an Npt (nitrophenylthio) side-chain functionality and bears a Boc (tert-butoxycarbonyl) protecting group on the amino nitrogen, with the D stereochemical form indicated by the D prefix. The molecule contains a free carboxylic acid (-COOH) alongside a Boc-protected amine (-NH-Boc), while the Npt substituent provides an aromatic, electron-withdrawing and sulfur-containing handle that can participate in conjugation or analytical derivatization depending on the experimental design. In peptide chemistry, Boc-protected amino acids such as this are used as building blocks for stepwise assembly of peptide chains and for preparing labeled or functionalized glycine-containing intermediates where the Npt group supports downstream chemical modification or detection.
CAT No: CP25165
CAS No:112695-98-4
Synonyms/Alias:Boc-D-NptGly-OH;112695-98-4;AmbotzBAA6290;Boc-D-t-butyl-alanine;AC1ODUN7;Boc-D-tert-butyl-alanine;SCHEMBL1360500;CTK8F0138;MolPort-006-705-600;PUQVQDMFCAGQQB-MRVPVSSYSA-N;ZINC2569779;AKOS015836516;RTR-002465;AM024621;N-(tert-butoxycarbonyl)-4-methyl-D-leucine;TR-002465;FT-0679740;N-tert-Butoxycarbonyl-3-tert-butyl-D-alanine;N-(tert-Butoxycarbonyl)-3-tert-butyl-D-alanine;N2-(tert-Butoxycarbonyl)-3-tert-butyl-D-alanine;I14-26474;D-Leucine,N-[(1,1-dimethylethoxy)carbonyl]-4-methyl-;(2R)-2-[(tert-butoxycarbonyl)amino]-4,4-dimethylpentanoicacid;(2R)-4,4-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoicacid;RAC-(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4,4-DIMETHYLPENTANOICACID
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-neopentylglycine, Boc-D-beta-tBu-Ala-OH
Boc-D-NptGly-OH is a Boc-protected D-configured glycine derivative bearing an Npt (naphthylmethyl/phenyl-type) side-chain substituent, provided as a protected amino acid building block for peptide assembly. The Boc group supports controlled N-terminus reactivity during peptide coupling, while the D stereocenter enables incorporation of non-proteinogenic stereochemistry into synthetic peptides for conformational and stability-focused studies. This protected form is typically selected when downstream peptide synthesis requires a reliable, isolable amino acid unit with defined reactivity and stereochemical identity.
1. Peptide Building Block Use
Boc-D-NptGly-OH is used by custom peptide synthesis groups and medicinal chemistry teams as a protected amino acid building block to introduce a D-configured glycine residue into peptide sequences. The Boc-protection pattern supports standard peptide coupling workflows where the N-terminus is managed to ensure chemoselective assembly of longer chains, including solution-phase and solid-phase peptide synthesis strategies. Researchers commonly select this specific derivative when they need the stereochemical inversion conferred by the D configuration and the distinctive Npt-containing side chain to tune local structure, steric environment, and physicochemical behavior of peptide analogs.
2. Peptidomimetic And SAR Studies
Boc-D-NptGly-OH supports peptidomimetic development and structure-activity relationship (SAR) programs where stereochemistry and side-chain identity are systematically varied to probe sequence-dependent properties. In medicinal chemistry research, the ability to incorporate a D-amino acid unit helps generate peptide analogs with altered conformational preferences and resistance to enzymatic processing, while the Npt substituent provides a hydrophobic/aromatic element that can influence binding-site interactions in receptor or protein-binding assay formats. This makes the reagent a practical choice for teams synthesizing focused libraries of analog peptides for lead optimization and mode-of-interaction exploration.
3. Pharmaceutical Intermediate Synthesis
Boc-D-NptGly-OH is also applied as a defined chiral amino acid intermediate for downstream pharmaceutical intermediate manufacturing, particularly when a protected D-amino acid motif is required as an input for larger synthetic sequences. Process and development chemists value the isolable Boc-protected format because it provides a controlled handle for sequential functionalization steps, enabling consistent handling of stereochemistry during scale-up-oriented synthesis planning. The Npt-bearing side-chain functionality further supports its use in constructing more complex intermediates used for peptide-like scaffolds and amino acid-derived fragments in industrial research settings.
4. Analytical Reference Material Preparation
Boc-D-NptGly-OH is frequently leveraged in laboratories that prepare analytical standards for method development and characterization of peptide-related intermediates and analogs. Because the compound is a stereochemically defined, protected amino acid building block, it can serve as a reference for LC-MS or other chromatographic workflows used to monitor peptide coupling outcomes, verify incorporation of the D-NptGly unit, and support impurity profiling during synthetic optimization. Analytical teams often choose this reagent when they need a structurally specific standard aligned with the exact protected building block used in the peptide synthesis route.
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