Boc-Val-Gly-OH is a protected amino acid derivative featuring a dipeptide-like structure composed of valine and glycine in which the N-terminus is masked as a Boc (tert-butoxycarbonyl) carbamate. The molecule bears a free C-terminal carboxylic acid (-COOH) and a valine side chain with an isopropyl substituent, while the Boc group suppresses the reactivity of the amino functionality toward undesired acylation or coupling. Boc-Val-Gly-OH is used as a stepwise building block in peptide synthesis and related derivatization workflows where controlled chemoselectivity of the free carboxyl group and the protected amine is required for constructing longer peptide chains.
CAT No: CP27132
CAS No:45233-75-8
Synonyms/Alias:BOC-VAL-GLY-OH;45233-75-8;(S)-2-(2-((tert-Butoxycarbonyl)amino)-3-methylbutanamido)aceticacid;SCHEMBL1003572;N-t-butoxycarbonyl-L-valylglycine;MolPort-027-845-008;ZINC2504758;6465AH;AKOS024258481;AJ-36041;AK158335;FT-0639846;K-9012;2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-methylbutanamido]aceticacid
Boc-Val-Gly-OH is a dipeptide-like amino acid derivative that combines an N-Boc-protected valine residue with a glycine carboxylic acid, yielding a chiral, peptide-compatible structure with a protected amide-forming nitrogen and an unprotected terminal carboxylic acid for further coupling. The Boc group on the valine nitrogen modulates nucleophilicity and enables controlled peptide bond formation under standard protected amino acid synthesis conditions, while the valine side chain introduces an isopropyl stereochemical environment that can influence conformational preferences in short peptides and peptidomimetics. The glycine segment provides a small, flexible backbone element that supports iterative chain elongation and downstream derivatization at the C-terminus. The presence of both a carbamate-protected amine and a free carboxyl group makes Boc-Val-Gly-OH a practical intermediate for protected amino acid chemistry, peptide building block preparation, and chiral fragment construction in synthetic organic and biochemical research workflows.
1. Peptide Synthesis
Boc-Val-Gly-OH supports peptide coupling workflows by presenting an N-Boc-protected valine nitrogen that can be deprotected when required to enable iterative amide bond formation, while the glycine carboxylic acid can participate in standard C-terminal activation chemistry. The valine stereocenter and isopropyl side chain provide a defined chiral motif that can be carried through to longer sequences, including short peptide scaffolds and sequence fragments used in library synthesis. The glycine unit contributes backbone flexibility that can reduce steric constraints during coupling and can be leveraged for constructing peptides with controlled local dynamics. Boc-Val-Gly-OH thus functions as a protected dipeptide intermediate for stepwise peptide assembly, including the preparation of analogs where terminal functionalization and controlled protection strategies are required.
2. Protected Amino Acid Chemistry
Boc-Val-Gly-OH is suitable for protected amino acid synthesis strategies where orthogonal functional group handling is required, because the Boc carbamate masks the valine amino functionality while leaving the terminal carboxylic acid available for further transformation. The combination of a protected amine and a free acid enables downstream conversion into activated esters, amides, or other C-terminal derivatives used to control peptide coupling directionality and prevent side reactions. The chiral valine residue provides a stereochemically defined intermediate that can be incorporated into chiral building block sequences without racemization under appropriately managed conditions. Boc-Val-Gly-OH can be employed as a process-relevant intermediate in fine chemical synthesis routes that require protected dipeptide fragments for controlled chain extension and purification-compatible handling.
3. SAR Studies
Boc-Val-Gly-OH can be applied in structure-activity relationship studies for generating peptide-based fragments and peptidomimetic building blocks that probe the influence of valine side-chain identity and glycine flexibility on molecular recognition. The defined valine stereochemistry and side-chain hydrophobicity enable systematic variation of local steric and electronic environments when incorporated into short analogs, while the glycine position allows modulation of backbone conformational freedom. The Boc-protected nitrogen and terminal carboxyl group support staged derivatization, enabling synthesis of series with consistent coupling points and controlled termini for comparative analytical characterization. Boc-Val-Gly-OH therefore serves as a chiral fragment precursor for SAR-oriented molecular design, including the preparation of standardized peptide segments used to map sequence-dependent effects.
4. Chemical Biology Labeling
Boc-Val-Gly-OH can be utilized in chemical biology workflows that require peptide fragment generation for conjugation and labeling, where the free C-terminal carboxylic acid enables attachment to linkers, tags, or immobilization handles. The Boc-protected valine nitrogen supports controlled deprotection timing, allowing the intermediate to be converted into a coupling-ready form while limiting undesired reactivity during intermediate storage and purification. The valine-glycine motif can function as a recognition-compatible segment in peptide conjugates, and the small glycine unit can help maintain accessibility of the conjugation site. Boc-Val-Gly-OH can be employed to produce labeled peptide derivatives used in biomolecule interaction studies, affinity reagent preparation, and analytical assay development requiring defined peptide stereochemistry.
5. Pharmaceutical Manufacturing
Boc-Val-Gly-OH is applicable to pharmaceutical manufacturing and related process chemistry as a protected peptide intermediate that can be incorporated into controlled synthetic routes for peptide-containing active ingredients or peptide-derived intermediates. The N-Boc protection strategy supports robust handling of the amine functionality during upstream processing, while the terminal carboxylic acid enables conversion into downstream coupling partners or salt/ester forms compatible with manufacturing logistics. The chiral valine residue provides a stereochemically defined unit that can be carried through to later stages of synthesis, supporting consistent impurity profiles associated with stereochemical integrity. Boc-Val-Gly-OH can be used as a building block in fine chemical synthesis and specialty chemical production where reproducible peptide bond formation and protected-group management are central to scale-up-compatible manufacturing design.
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