H-Aib-OH is an unprotected α-aminoisobutyric acid (Aib) derivative featuring a free amino group and a free carboxyl group attached to an α-carbon bearing the characteristic gem-dimethyl side chain. The molecule is a neutral amino acid in which the side chain consists of two methyl substituents, giving a sterically hindered, conformationally restrictive profile relative to less substituted amino acids, while retaining the standard amino acid backbone functionality. H-Aib-OH is used as a building block for preparing Aib-containing peptides and peptide analogues in solution-phase or solid-phase synthesis, and it can also serve in structure-property studies where steric effects and backbone conformational preferences are examined.
CAT No: CP25950
CAS No:62-57-7
Chemical Name:2-Amino-isobutyric acid, 2-Methylalanine
H-Aib-OH is an α-aminoisobutyric acid (Aib) derivative presented as the free amino acid, featuring a chiral center at the α-carbon and a sterically hindered side chain composed of two methyl groups. The molecule contains a primary amine and a carboxylic acid that can participate in standard amino acid coupling, salt formation, and acid-base controlled transformations, while the gem-dimethyl motif strongly biases conformational preferences toward 3.10- and 13-helix-like structures in peptide contexts. The absence of built-in N- or C-terminal protecting groups means H-Aib-OH can be directly converted into protected amino acid derivatives for peptide assembly, or used as a chemically defined feedstock for downstream derivatization. The stereochemical integrity of the α-center supports stereocontrolled incorporation into peptide building blocks and chiral synthetic sequences where Aib is used to modulate backbone rigidity and molecular recognition.
1. Peptide Synthesis
H-Aib-OH is used in peptide synthesis workflows as an Aib residue precursor for constructing conformationally constrained peptide segments. The free amine and carboxylic acid functional groups enable conversion into N-protected and/or activated forms that are compatible with amide bond formation strategies used in stepwise peptide assembly. The α-amino acid stereocenter supports stereodefined coupling, while the gem-dimethyl side chain can be incorporated to enhance helix propensity and reduce backbone flexibility in peptide analogs. Downstream, H-Aib-OH-derived protected intermediates can be assembled into peptides for scaffold generation, peptide library construction, and structure-activity relationship studies.
2. Peptidomimetics Research
H-Aib-OH is applied in peptidomimetic and molecular scaffold design where backbone rigidity is a key design variable. The amino acid backbone provides a handle for forming amide-linked analogs, and the steric bulk of the Aib side chain can be leveraged to tune conformational landscapes of peptide mimics. Derivatization of the free functional groups into protected amino acid derivatives enables systematic variation of N-terminus and C-terminus chemistry while maintaining the Aib stereochemical configuration. Resulting Aib-containing mimetics can serve as research-grade intermediates for studying binding conformations, protease resistance trends, and backbone-dependent molecular recognition.
3. Chiral Building Block Development
H-Aib-OH functions as a chiral amino acid intermediate for preparing enantiopure derivatives used in stereoselective synthesis. The molecule's α-amino acid functionality allows formation of N-protected amino acid derivatives and ester or activated carboxyl derivatives that can participate in chiral coupling sequences and downstream functional group interconversions. The gem-dimethyl side chain provides a sterically defined environment that can influence reactivity and selectivity during protection, activation, and coupling steps. Prepared derivatives from H-Aib-OH can be used as building blocks for asymmetric synthesis programs, chiral library generation, and stereochemically controlled peptide construction.
4. Chemical Biology Labeling
H-Aib-OH can be employed in chemical biology research to introduce Aib residues into biomolecule-reactive peptide constructs used for labeling and probe development. The free amino and carboxyl groups support transformation into protected intermediates that can be coupled into peptide tags, linkers, or recognition elements while preserving the Aib stereocenter. Side-chain steric properties can help stabilize defined conformations of labeling peptides, which may improve reproducibility of structure-dependent conjugation chemistry. Downstream derivatives generated from H-Aib-OH can be incorporated into bioconjugation-ready peptide intermediates for analytical assays and molecular interaction studies.
5. Process Chemistry Intermediate
H-Aib-OH is suitable for process chemistry and fine chemical synthesis as a defined amino acid feedstock for manufacturing protected Aib derivatives and activated coupling partners. The presence of both amine and carboxylic acid groups enables controlled salt formation and straightforward conversion into N-protected forms and carboxyl-activated intermediates used in industrial peptide building block production. The sterically hindered gem-dimethyl side chain provides a consistent structural motif that can be carried through manufacturing routes to yield reproducible peptide coupling inputs. Downstream, H-Aib-OH-derived intermediates support scalable preparation of Aib-containing peptide reagents used across peptide manufacturing, specialized chemical production, and industrial chemical supply chains.
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