Boc-7-Aminoheptanoic acid is a protected, non-natural amino acid derivative featuring a seven-carbon aliphatic chain bearing a terminal primary amino group and a carboxylic acid functionality, with the amino group protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule contains the Boc-protected amine and an unprotected carboxylic acid, and its linear hydrophobic side chain provides a spacer-like handle for building peptide backbones or for preparing amide-linked conjugates. In synthesis, the Boc group supports chemoselective handling of the amino functionality during stepwise coupling strategies, while the free carboxyl group enables formation of peptide bonds or other carboxyl-derived linkages for structure-activity studies and the preparation of more complex amino acid derivatives.
CAT No: CP03702
CAS No:60142-89-4
Synonyms/Alias:D-Glutamicacid-gamma-4-nitroanilide;60133-17-7;H-D-Glu(pNA)-OH;AC1OF0UH;ZINC4069929;AKOS015910598;FT-0640661;I14-40811;(2R)-2-amino-5-(4-nitroanilino)-5-oxopentanoicacid
Boc-7-Aminoheptanoic acid is a Boc-protected amino acid building block featuring a linear seven-carbon side chain (heptyl) that provides hydrophobic character for peptide and peptidomimetic design. The tert-butoxycarbonyl (Boc) group on the amino functionality makes it a protected amino acid intermediate commonly used in controlled peptide assembly workflows, while the carboxylic acid enables downstream activation and coupling to form amide bonds. Its straightforward aliphatic topology makes it useful when longer hydrophobic spacers or flexible linkers are required in synthetic targets.
1. Peptide Coupling Building Block
Boc-7-Aminoheptanoic acid is used by peptide synthesis groups to introduce a hydrophobic heptyl side chain at a defined position within peptide sequences, especially when flexible, aliphatic spacing is needed for structure-function studies. Researchers in academic peptide chemistry and industry custom peptide manufacturing rely on Boc-protected amino acid intermediates to manage chemoselectivity during stepwise assembly, using the Boc-protected amine to prevent premature side reactions while the carboxylic acid is carried through activation/coupling steps. This product is also a practical choice for preparing modified peptide segments and for generating longer-chain amino acid residues that are not always available as unprotected building blocks in standard peptide catalogs.
2. Peptidomimetic And Linker Design
Boc-7-Aminoheptanoic acid supports peptidomimetic development and medicinal chemistry programs that require hydrophobic spacers to tune conformation, solubility balance, or membrane-interaction properties in synthetic analogs. Medicinal chemistry teams often incorporate aliphatic, non-aromatic chain segments to modulate the presentation of functional motifs while maintaining a peptide-like amide backbone. In these workflows, the protected amino acid form simplifies incorporation into larger synthetic sequences by providing a reliable amine protection strategy during intermediate construction, enabling the heptanoic side chain to be installed as a defined structural element within ligands, scaffold fragments, and SAR libraries.
3. Pharmaceutical Intermediate Synthesis
Boc-7-Aminoheptanoic acid is frequently used as a pharmaceutical intermediate building block for constructing longer-chain aliphatic amide motifs used in process chemistry and specialty chemical manufacturing. Process development chemists value Boc-protected amino acid intermediates as controllable, isolable units that can be converted into activated derivatives for subsequent coupling steps toward target intermediates. The linear C7 side chain is particularly relevant for generating hydrophobic linker fragments and spacer units that appear in many synthetic programs, including the preparation of amide-containing intermediates used to assemble larger molecules in a modular fashion.
4. Solid-Phase Segment Assembly
Boc-7-Aminoheptanoic acid can be employed in segment-based peptide assembly workflows where protected amino acid residues are introduced as discrete building blocks, including strategies that prepare amino acid segments for later ligation or coupling. Peptide synthesis teams that build longer constructs often prefer protected amino acids to ensure that only the intended functional group participates at each step, improving the robustness of multi-step assembly. The combination of a Boc-protected amine and a carboxylic acid functionality makes it a practical intermediate for preparing heptyl-containing peptide segments, which are commonly used in structure-guided studies, materials peptide precursors, and synthetic peptide standards.
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