D(-)-Ac-alpha-phenylglycinol is an amino alcohol derivative of phenylglycine featuring a primary amino group and a hydroxymethyl (alcohol) functionality at the alpha position relative to the phenyl-substituted carbon framework. The molecule bears a benzyl-like phenyl side chain and exists in the D(-) stereochemical form as indicated by the product name, with the amino and alcohol groups providing two distinct hydrogen-bonding and derivatization handles. As a chiral building block for peptide and peptidomimetic synthesis, it can be employed to prepare amino alcohol-containing analogues, support structure-activity studies, and enable chemical labeling or conjugation strategies that rely on the orthogonal reactivity of the amine and alcohol.
CAT No: CP27478
CAS No:78761-26-9
Synonyms/Alias:Ac-D-phenylglycinol;78761-26-9;N-ACETYL-D-PHENYLGLYCINOL;D(-)-Ac-alpha-phenylglycinol;SCHEMBL8582093;CTK8F7493;D-AC-ALPHA-PHENYLGLYCINOL;ZINC2391134;7509AH;KM1942;AKOS006272900;FT-0641691;(?)-N-[(R)-alpha-(Hydroxymethyl)benzyl]acetamide
D(-)-Ac-alpha-phenylglycinol is a chiral amino alcohol derived from phenylglycine, featuring a stereogenic center at the alpha position and a primary alcohol that can participate in hydrogen bonding and stereocontrolled derivatization. The molecule contains a secondary amine (or protected amine depending on handling) and a benzylic phenyl substituent that together support formation of imines, carbamates, and amide-linked derivatives used in asymmetric synthesis. The amino alcohol motif enables selective functional group interconversions, including conversion of the hydroxyl to leaving groups or protecting-group derivatives and controlled transformation of the amine for peptide coupling chemistry. As a chiral intermediate, D(-)-Ac-alpha-phenylglycinol is suited to downstream construction of amino acid derivatives, chiral auxiliaries, and peptide-related building blocks through standard protecting-group strategies and stereochemically aware synthetic sequences.
1. Chiral Building Blocks
D(-)-Ac-alpha-phenylglycinol supports chiral synthesis workflows where an amino alcohol provides a stereodefined handle for further functionalization. The alpha-amino and hydroxyl functionalities enable formation of protected amino derivatives, such as carbamate-protected amines and ester- or ether-protected alcohols, which can be carried through multi-step sequences without racemization at the stereocenter. The benzylic phenyl group provides a rigid, conformationally informative substituent that can influence diastereoselective transformations during derivatization. Chiral amino alcohol derivatives prepared from this scaffold can serve as intermediates for enantioenriched amino acid analogs, chiral auxiliaries, and stereocontrolled ligand or catalyst precursors used in fine chemical synthesis.
2. Peptidomimetic Synthesis
D(-)-Ac-alpha-phenylglycinol is applicable to peptidomimetic construction where amino alcohol geometry can be translated into constrained backbone surrogates. The presence of a stereogenic alpha center and a nucleophilic amine allows conversion into amide-forming intermediates, while the hydroxyl can be functionalized to support cyclization, ether/ester formation, or attachment of side-chain fragments. Protecting-group strategies that differentiate the amine and alcohol enable sequential coupling and selective deprotection, supporting synthesis of amino acid mimics used to probe conformational effects in peptide-like scaffolds. Downstream products derived from this intermediate can be incorporated into synthetic libraries for structure-activity relationship studies and molecular design efforts focused on backbone constraint and stereochemical recognition.
3. Protected Amino Derivatives
D(-)-Ac-alpha-phenylglycinol functions as a chiral starting point for preparing protected amino acid derivatives and peptide coupling-ready intermediates. The amino alcohol can be converted into N-protected forms and, where required, into C-functionalized derivatives by transforming the hydroxyl into an activated ester, carbonate, or other protected group compatible with peptide coupling conditions. Stereochemical integrity is maintained by selecting protection and activation chemistries that avoid conditions promoting epimerization at the alpha carbon. The resulting protected intermediates can then be used for subsequent amide bond formation, enabling incorporation into peptide synthesis routes or the generation of amino acid ester and amide derivatives used in biochemical research intermediate preparation.
4. Chemical Biology Probes
D(-)-Ac-alpha-phenylglycinol can be employed in chemical biology research to generate chiral amino alcohol-based probes and labeled derivatives. The amine enables attachment handles for conjugation chemistry, while the hydroxyl can be functionalized to introduce linkers, fluorophore-reactive groups, or affinity tags through controlled protection and deprotection sequences. The stereodefined center and phenylglycinol framework can influence binding orientation when probes are designed to mimic amino acid recognition elements. Labeled or derivatized products prepared from this intermediate can be used as molecular tools for studying biomolecular interactions, enabling downstream analytical characterization and targeted biomolecule modification strategies.
5. Process Chemistry Intermediate
D(-)-Ac-alpha-phenylglycinol is suitable for process chemistry intermediate development where a stable chiral amino alcohol can be routed into multiple downstream products. The functional group set supports scalable protection-group management, including selective formation of N- and O-protected derivatives that can be processed through standard intermediate purification and conversion steps. The benzylic phenyl substituent and the defined stereocenter provide a consistent chemical identity for manufacturing routes aimed at producing enantioenriched amino acid derivatives, peptidomimetic precursors, or specialty chiral building blocks. Conversion of the hydroxyl into protected or activated forms can be integrated into industrial synthetic sequences to streamline downstream coupling and reduce variability in intermediate handling.
6. Analytical Standards And Characterization
D(-)-Ac-alpha-phenylglycinol serves as a reference material for analytical method development and stereochemical characterization of amino alcohol derivatives. The defined chirality and functional groups allow formation of derivatization products used in chromatographic separation, including diastereomeric derivatives generated through selective reaction at the amine or hydroxyl. The phenylglycinol scaffold provides distinct spectroscopic and chromatographic signatures that can support identity confirmation for related intermediates in peptide synthesis and amino acid derivatization workflows. Reference standards derived from this compound can also support quality control for protected amino derivatives and downstream peptidomimetic intermediates where stereochemical purity and functional group integrity are critical.
3. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
5. 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