H-L-Dab(Boc)-OMe*HCl

H-L-Dab(Boc)-OMe*HCl is an L-2,4-diaminobutyric acid derivative presented as a methyl ester hydrochloride, where the side-chain amino group is protected as a Boc carbamate and the free amino functionality is present as a salt. The molecule therefore contains a chiral amino acid core bearing a stereogenic center, a methyl ester at the carboxyl terminus, and two nitrogen functionalities with distinct reactivity profiles: a Boc-protected amine that is stable under many peptide-coupling conditions and a salt-associated amine that can be unmasked for selective coupling. The hydrochloride counterion increases handling robustness and supports controlled deprotection and derivatization strategies, while the ester functionality can participate in downstream transformations toward carboxylic acid or activated ester forms. As a chiral amino acid ester with orthogonally protected amines, this compound functions as a practical intermediate for protected amino acid synthesis and peptide building block preparation in both research and manufacturing workflows.

1. Protected Amino Acids

H-L-Dab(Boc)-OMe*HCl is used in protected amino acid chemistry and chiral intermediate preparation because its methyl ester and Boc carbamate enable staged functional group manipulation. The Boc-protected side-chain amine tolerates common peptide coupling reagents, while the ester and salt-associated amino group can be converted into coupling-ready forms through controlled deprotection and ester-to-acid activation sequences. The presence of a defined stereocenter supports stereochemically consistent incorporation into peptide sequences and amino acid derivatives. Downstream processing can generate N- and C-functionalized Dab-based intermediates suited for fine chemical synthesis and peptide building block supply.

2. Peptide Synthesis

H-L-Dab(Boc)-OMe*HCl supports peptide coupling chemistry where orthogonal nitrogen protection is required for selective formation of amide bonds. The Boc group on the side-chain amine can be maintained during N-terminal activation steps, allowing controlled assembly of peptide fragments without undesired cross-linking or oligomerization from free amine reactivity. The methyl ester can be transformed into a carboxylate equivalent suitable for coupling, enabling construction of Dab-containing peptides and peptidomimetic scaffolds with predictable side-chain functionality. The hydrochloride salt form also facilitates reproducible handling during synthesis planning, aligning with peptide building block preparation for both academic and industrial peptide manufacturing.

3. Bioconjugation Chemistry

H-L-Dab(Boc)-OMe*HCl is applicable to chemical biology and bioconjugation workflows that require amino acid-derived linkers with orthogonally addressable amines. The protected side-chain Boc carbamate can be deprotected to reveal a second primary amine for conjugation chemistry, while the amino acid backbone provides a chiral, well-defined scaffold for attachment to biomolecule-reactive handles. The methyl ester functionality can be converted into carboxylic acid derivatives or activated intermediates that participate in amide-forming conjugation strategies. The resulting Dab-based conjugation intermediates can be used for generating labeled biomolecule analogs and for constructing multi-functional linkers in applied peptide science.

4. Peptidomimetics And SAR

H-L-Dab(Boc)-OMe*HCl is suited for peptidomimetic construction and structure-activity relationship studies where side-chain diamine presentation influences molecular recognition. The Dab side chain provides an additional nitrogen for tuning hydrogen-bonding patterns and for introducing further derivatization handles after selective Boc removal. The stereogenic amino acid core enables synthesis of constrained or stereochemically defined analogs used to probe how spacing and protonation states affect binding motifs in SAR campaigns. The compound's protected amine and ester-to-carboxyl conversion potential make it a practical intermediate for generating libraries of functionalized amino acid derivatives and SAR-focused building blocks.

5. Process Chemistry Intermediates

H-L-Dab(Boc)-OMe*HCl can be employed as a manufacturing intermediate in process chemistry for amino acid derivative production, where orthogonal protection improves route control and minimizes side reactions. The Boc-protected side-chain amine and methyl ester provide discrete functional-group "switches" that can be addressed in sequence to design scalable synthetic operations for Dab-based building blocks. The hydrochloride salt form supports stable storage and controlled reactivity during intermediate handling, while the defined stereochemistry reduces the need for extensive stereochemical correction downstream. The compound can therefore serve as a chiral amino acid ester platform for producing protected amino acids, peptide coupling reagents, and downstream fine chemical intermediates used in industrial amino acid and peptide supply chains.

1. Effect of Probiotic Lactobacillus plantarum on Streptococcus mutans and Candida albicans Clinical Isolates from Children with Early Childhood Caries

2. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists

3. The effect of B-type allatostatin neuropeptides on crosstalk between the insect immune response and cold tolerance

4. cRGD-functionalized, DOX-conjugated, and 64Cu-labeled superparamagnetic iron oxide nanoparticles for targeted anticancer drug delivery and PET/MR imaging

5. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line