Boc-L-Igl-OH

Boc-L-Igl-OH is a Boc-protected amino acid derivative in which the amino acid portion corresponds to L-Igl (Igl) bearing a free carboxylic acid. The molecule contains a tert-butoxycarbonyl (Boc) carbamate protecting group on the amino functionality, while the side chain of Igl provides its characteristic functional group for incorporation into peptide frameworks. As a protected building block, it is used in peptide synthesis workflows to support chemoselective coupling at the carboxyl group while the Boc group helps suppress undesired reactions of the amino terminus during stepwise assembly.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25487

CAS No:181227-47-4

Synonyms/Alias:181227-47-4;(S)-N-Boc-2-indanylglycine;(S)-2-((tert-Butoxycarbonyl)amino)-2-(2,3-dihydro-1H-inden-2-yl)aceticacid;Boc-(2-indanyl)-Gly-OH;(S)-[(tert-butoxycarbonyl)amino](2,3-dihydro-1H-inden-2-yl)aceticacid;AmbotzBAA1388;Boc-L-2-indanyglycine;PubChem23310;SCHEMBL5389519;CTK8B9017;MolPort-002-344-048;ZINC2567258;ANW-61826;AKOS015909033;RTR-008327;AJ-41374;AK106971;AM007605;AN-30590;KB-210877;TR-008327;A4017;FT-0679751;I14-33284;(2S)-2-(tert-butoxycarbonylamino)-2-indan-2-yl-aceticacid

Chemical Name:N-alpha-t-Butyloxycarbonyl-2-indanyl-L-glycine, (S)-2-(t-Butyloxycarbonylamino)-2-(2,3-dihydro-1H-inden-2-yl)acetic acid

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M.F/Formula
C16H21NO4
M.W/Mr.
291,35 g/mole

Boc-L-Igl-OH is a Boc-protected L-amino acid building block featuring an isoleucine-like, branched side chain and a tert-butoxycarbonyl (Boc) group on the amino functionality. As a protected amino acid, it is primarily used to assemble defined peptide segments and to prepare intermediates where controlled reactivity and compatibility with peptide coupling workflows are required. The free carboxylic acid (as the acid form) supports downstream activation for peptide bond formation while the Boc group provides amino protection during synthesis.

1. Peptide Segment Building

Boc-L-Igl-OH is used by peptide synthesis groups to incorporate this specific L-amino acid residue into peptide sequences where a branched side chain is required for steric and conformational effects. Custom peptide manufacturers and academic peptide chemistry labs rely on Boc-protected amino acids like this to build well-defined peptide segments by coupling the amino acid's carboxyl group to an appropriately protected amine on the growing chain. The Boc protection helps maintain chemoselectivity during repeated coupling and deprotection cycles, supporting the preparation of peptides for structure-activity relationship studies and receptor/ligand chemistry.

2. Solution-Phase Peptide Synthesis

Boc-L-Igl-OH is frequently selected for solution-phase peptide synthesis workflows that use Boc-based protection strategies and stepwise segment assembly. Medicinal chemistry groups developing peptidomimetic leads often prefer protected amino acid building blocks that integrate cleanly into established coupling/deprotection schedules, enabling the rapid generation of analog libraries with controlled sequence composition. In this context, the free carboxylic acid form is advantageous for activation and coupling to protected amines, while the Boc group on the amino terminus ensures the residue remains protected until the intended deprotection step.

3. Pharmaceutical Intermediate Development

Boc-L-Igl-OH also serves as a specialized intermediate for downstream synthesis of peptide-derived scaffolds and related medicinal chemistry intermediates. Process and discovery chemistry teams use amino acid building blocks to prepare defined fragments that can be further elaborated into larger constructs such as peptide conjugates, constrained peptide analogs, or advanced coupling partners for final assembly. The protected nature of this reagent supports controlled handling and minimizes undesired side reactions during multi-step intermediate preparation, which is particularly valuable when building complex, sequence-defined structures.

4. Peptide Library Analog Production

Boc-L-Igl-OH is commonly employed in peptide library production where residue-level variation is used to probe structure-property relationships. Peptide screening groups and chemical biology laboratories incorporate this building block into parallel synthesis campaigns to generate analog sets that differ by one or more amino acid positions, allowing systematic evaluation of how side-chain branching influences peptide conformation, local interactions, and overall physicochemical behavior. The defined stereochemistry and Boc protection pattern make it a practical choice for reproducible incorporation into library members using standardized peptide assembly protocols.

Size
1 g;5 g;
InChI
1S/C16H21NO4/c1-16(2,3)21-15(20)17-13(14(18)19)12-8-10-6-4-5-7-11(10)9-12/h4-7,12-13H,8-9H2,1-3H3,(H,17,20)(H,18,19)/t13-/m0/s1
InChI Key
VCHHRDDQOOBPTC-ZDUSSCGKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(C1CC2=CC=CC=C2C1)C(=O)O

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