Boc-D-Igl-OH is a protected, non-proteinogenic amino acid derivative featuring the D-configured Igl (Iglutamine-like) amino acid core bearing a Boc (tert-butoxycarbonyl) protecting group on the amino functionality. The molecule contains a free carboxylic acid group and a Boc-carbamate-protected amino group, with the side chain presenting the characteristic functionality of the Igl residue that can be used as a structural element in peptide-related syntheses. Boc-D-Igl-OH is employed as a stepwise building block in protected amino acid chemistry, including solid-phase or solution-phase peptide synthesis workflows where temporary amino protection helps control chemoselectivity during coupling and subsequent deprotection.
CAT No: CP25488
CAS No:181227-48-5
Synonyms/Alias:Boc-D-Igl-OH;181227-48-5;AmbotzBAA1343;Boc-d-(2-inda)gly-oh;SCHEMBL1598690;CTK8F0531;MolPort-002-345-299;VCHHRDDQOOBPTC-CYBMUJFWSA-N;ZINC2567264;AKOS025312271;RTR-008328;TR-008328;FT-0679742;V3911;(2R)-[(tert-butoxycarbonyl)amino](2,3-dihydro-1H-inden-2-yl)ethanoicacid;(2R)-[(tert-butoxycarbonyl)amino](2,3dihydro-1H-inden-2-yl)ethanoicacid;(R)-[(tert-butoxycarbonyl)amino](2,3-dihydro-1H-inden-2-yl)aceticacid;(2R)-2,3-dihydro-1H-inden-2-yl({[(1,1-dimethylethyl)-oxy]carbonyl}amino)ethanoicacid;(2R)-2,3-Dihydro-1H-inden-2-yl({[(1,1-dimethylethyl)oxy]-carbonyl}amino)ethanoicacid;(2R)-2,3-dihydro-1H-inden-2-yl({[(1,1-dimethylethyl)oxy]carbonyl}-amino)-ethanoicacid;(2R)-2,3-dihydro-1H-inden-2-yl({[(1,1-dimethylethyl)oxy]carbonyl}-amino)ethanoicacid;(2R)-2,3-Dihydro-1H-inden-2-yl({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethanoicacid;(R)-2-(tert-butyloxycarbonylamino)-2-(2,3-dihydro-1H-inden-2-yl)aceticacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-2-indanyl-D-glycine, (R)-2-(t-Butyloxycarbonylamino)-2-(2,3-dihydro-1H-inden-2-yl)acetic acid
Boc-D-Igl-OH is a Boc-protected D-amino acid building block featuring the Igl side chain, supplied in a protected carboxylic acid form suitable for peptide assembly. The stereochemical D-configuration and the N-terminal Boc protection make it a practical reagent for constructing stereochemically defined peptide segments and for preparing modified peptide intermediates where side-chain identity must be preserved during coupling and purification.
1. Solid-Phase Peptide Synthesis
Boc-D-Igl-OH is used by peptide synthesis groups as a protected, stereodefined amino acid building block for solid-phase peptide synthesis workflows, particularly when the Igl residue is required at a specific position in a peptide sequence. The Boc group supports controlled peptide chain assembly under standard protected-amino-acid handling practices, helping researchers build peptides with defined stereochemistry and side-chain composition for downstream studies such as structure-activity relationship campaigns and sequence optimization.
2. Peptide Segment Building Block
Boc-D-Igl-OH serves as a reliable component for preparing peptide segments in solution-phase or convergent assembly strategies, where a single protected residue is incorporated into a larger intermediate prior to final coupling. Medicinal chemistry and peptide development teams commonly select Boc-protected amino acids like this to maintain residue integrity through multi-step synthesis, enabling the preparation of stereochemically consistent intermediates for custom peptide manufacturing and library synthesis.
3. Stereodefined SAR Peptide Libraries
Boc-D-Igl-OH is frequently employed in research settings that require systematic variation of peptide sequences while holding other stereochemical elements constant, such as SAR-driven library construction. By providing a D-configured, Boc-protected Igl residue, it supports the generation of peptide analog panels used in chemical biology and protein chemistry programs to evaluate how specific stereochemistry and side-chain identity influence peptide properties, including conformational behavior and sequence-dependent performance in assay formats.
4. Pharmaceutical Intermediate Development
Boc-D-Igl-OH is also used as a protected amino acid intermediate in the upstream development of peptide-based drug candidates and related lead optimization materials, where defined building blocks are required to produce advanced intermediates. Process development and CMC-oriented synthesis groups value Boc-protected amino acids for their role in controlled stepwise assembly, supporting the preparation of well-defined, stereochemically consistent intermediates that can be carried forward into larger synthetic campaigns.
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