DL-3-(3-benzofuranyl)-Alanine is a non-natural, benzofuran-substituted alanine derivative in which the alanine backbone bears a 3-(3-benzofuranyl) side chain, classifying it as an amino acid analogue suitable for incorporation into peptide-like structures. The molecule contains both an amino group and a carboxyl group on the α-carbon framework, with the benzofuran ring providing a hydrophobic, aromatic functionality; the "DL" designation indicates a racemic mixture of stereoisomers at the α-position. As an amino acid analogue, it is used in peptide synthesis and structure-activity studies to introduce a benzofuran-containing side chain for probing binding, conformational effects, and labeling or conjugation strategies that rely on aromatic scaffold presentation.
CAT No: CP20601
DL-3-(3-benzofuranyl)-Alanine is a racemic alanine derivative in which the β-carbon bears a 3-benzofuranyl substituent, generating a chiral center at the amino acid backbone while the product is supplied as a DL mixture. The molecule contains a primary amino group and a carboxylic acid (or acid-equivalent functionality depending on the supplier form), enabling standard amino acid chemistry such as amide formation, esterification, and side-chain derivatization. The benzofuran ring contributes an aromatic heterocycle with distinct electronic properties and potential for π-stacking interactions, making it relevant for medicinal chemistry scaffolds and peptide/peptidomimetic analogs. The combined amino acid functionality and heteroaromatic side chain support conversion into protected amino acid derivatives and downstream coupling partners for synthetic and biochemical research workflows.
1. Peptide Building Block
DL-3-(3-benzofuranyl)-Alanine is applied in peptide synthesis workflows as an alanine-based building block for incorporating a benzofuran-containing residue into peptide chains. The amino and carboxyl functionalities can be converted into N-protected and activated forms to enable peptide coupling chemistry, while the benzofuran side chain remains chemically stable under typical peptide coupling conditions and can influence conformational preferences. Racemic stereochemistry can be leveraged for generating libraries of peptide analogs when stereochemical resolution is not required at the screening stage, or when subsequent separation is planned. Downstream use includes preparation of peptidomimetic peptides and heteroaromatic-substituted sequences for structure-activity relationship studies and binding-mode investigations.
2. Chiral Amino Acid Intermediate
DL-3-(3-benzofuranyl)-Alanine serves as a chiral amino acid intermediate platform for stereocontrolled synthesis of enantiopure derivatives when resolution or asymmetric derivatization is employed upstream. The alanine backbone provides a defined handle for introducing stereochemical control at the α-carbon, while the benzofuran substituent offers a robust aromatic heterocycle that can survive multiple protection and activation steps. N-protection of the amino group and conversion of the carboxyl group to an ester or activated acid derivative can support iterative synthetic sequences that require predictable functional group behavior. Resulting intermediates can feed into downstream synthesis of enantiopure benzofuran-containing amino acid analogs used in medicinal chemistry and peptide chemistry programs.
3. Peptidomimetic SAR Studies
DL-3-(3-benzofuranyl)-Alanine is utilized in peptidomimetic and SAR (structure-activity relationship) studies where heteroaromatic side chains are incorporated to modulate binding interactions and metabolic stability. The benzofuran ring can participate in hydrophobic and π-interaction networks, while the amino acid framework supports conversion into amide-linked analogs that mimic peptide backbone features. Functional group interconversions such as N-alkylation, N-acylation, or carboxyl activation enable rapid generation of derivative series for SAR mapping, including analogs with modified termini or altered linker chemistry. The compound's compatibility with standard amino acid derivatization strategies supports systematic exploration of structure-function relationships in synthetic organic chemistry and chemical biology research.
4. Chemical Biology Probes
DL-3-(3-benzofuranyl)-Alanine can be applied to chemical biology research as a scaffold for building conjugatable amino acid derivatives used in biomolecule labeling and molecular recognition studies. The amino acid functionality supports installation of orthogonal protecting groups and subsequent deprotection to generate reactive intermediates for coupling to targeting ligands, linkers, or reporter moieties. The benzofuran heteroaromatic side chain can serve as a recognition element or as a hydrophobic anchor within probe designs, enabling incorporation into peptide-like constructs that interact with protein binding sites. Downstream formation of labeled or functionalized analogs supports analytical method development, binding assays, and probe optimization efforts within biochemical research workflows.
5. Pharmaceutical Intermediate Preparation
DL-3-(3-benzofuranyl)-Alanine is suitable for pharmaceutical intermediate preparation where amino acid-derived heteroaromatic motifs are used to construct small-molecule and peptide-like candidates. The presence of an amino acid backbone enables conversion to protected amino acid derivatives and activated carboxyl intermediates that participate in amide bond formation, N-substitution, and fragment assembly. The benzofuran ring provides a stable aromatic heterocycle that can be retained through multi-step synthesis while contributing defined physicochemical characteristics relevant to medicinal chemistry. Resulting intermediates can be routed into fine chemical synthesis for generating drug discovery scaffolds, including termini-modified analogs and heteroaromatic-containing building blocks for further derivatization.
1. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More