Fmoc-L-allo-threoninol is an Fmoc-protected amino alcohol derivative of the threoninol family, featuring the L-allo stereochemical designation and a side chain consistent with a β-hydroxy amino alcohol scaffold rather than a standard proteinogenic amino acid. The molecule contains an Fmoc carbamate protecting group on the amino functionality while the primary alcohol and the side-chain hydroxyl provide hydrogen-bonding and polarity, and the carboxyl group is replaced by the alcohol-bearing threoninol framework. In peptide and amino-alcohol chemistry, this protected building block is used as a precursor for assembling modified peptide backbones or for introducing hydroxyl-bearing amino alcohol residues into synthetic constructs via controlled incorporation of the protected nitrogen.
CAT No: CP26871
CAS No:252049-03-9
Synonyms/Alias:FMOC-L-ALLO-THREONINOL;252049-03-9;CTK4F5204;ZINC2244301;6916AH;ZINC02244301;AKOS015909104;I14-33049;Carbamicacid,[(1S,2S)-2-hydroxy-1-(hydroxymethyl)propyl]-,9H-fluoren-9-ylmethylester(9CI)
Fmoc-L-allo-threoninol is an Fmoc-protected L-allo threonine-derived amino alcohol that retains a stereogenic center within the side-chain and presents a primary alcohol at the terminus, enabling amino acid modification chemistry and peptide-compatible coupling strategies. The molecule combines an N-Fmoc carbamate-protected amine with a free hydroxymethyl group, yielding a protected amino alcohol building block whose polarity and hydrogen-bonding profile differ from standard threonine derivatives. The allo stereochemistry governs the relative three-dimensional arrangement of the side-chain hydroxyl and the backbone, which can influence conformational preferences during peptide assembly and downstream derivatization. The presence of both a protected nitrogen and an unprotected alcohol makes the compound suitable for sequential protection/deprotection workflows, including orthogonal functional group transformations that feed into peptide analog construction and synthetic intermediate preparation.
1. Peptide Synthesis
Fmoc-L-allo-threoninol is used in peptide synthesis workflows where an amino alcohol side-chain is required, such as constructing threoninol-containing fragments for peptide building block preparation and N-terminal or internal residue incorporation. The Fmoc-protected carbamate enables standard base-labile deprotection to reveal the amino group for coupling, while the free primary alcohol supports controlled side-chain functionalization after assembly. The allo stereochemistry can be leveraged to access stereodefined peptide analogs with defined spatial orientation of the hydroxymethyl group, supporting structure-activity relationship studies of side-chain geometry. The resulting threoninol-containing peptides can be further modified through alcohol derivatization, enabling downstream generation of constrained analogs, conjugation handles, or protected variants for iterative synthesis.
2. Amino Acid Derivatization
Fmoc-L-allo-threoninol serves as a chiral amino alcohol intermediate for amino acid derivatization and protected amino acid synthesis routes that require orthogonal reactivity between the nitrogen and the hydroxyl group. The Fmoc group provides a stable handle for N-protection during chemical transformations, while the primary alcohol can undergo selective protection (e.g., etherification or esterification) or functional group conversion to introduce leaving groups, carbonyl derivatives, or linkers. The stereogenic arrangement characteristic of the L-allo configuration supports stereoselective downstream chemistry, including formation of diastereomerically defined intermediates for fine chemical synthesis. The compound can be employed to prepare C-terminal modification precursors and side-chain functionalized amino acid analogs that feed into peptide coupling chemistry and scaffold diversification.
3. Chemical Biology Probes
Fmoc-L-allo-threoninol is suitable for chemical biology research requiring amino alcohol-containing probes that mimic threonine-like hydrogen-bonding while providing a reactive hydroxymethyl handle for labeling chemistry. The Fmoc-protected amine supports incorporation into peptide-like constructs, whereas the free alcohol can be converted into conjugation-ready motifs such as activated ethers, ester linkers, or orthogonally protected groups for sequential bioconjugation steps. The defined allo stereochemistry can influence probe recognition in binding assays that depend on side-chain orientation and local hydration patterns. The resulting labeled or derivatized amino acid derivatives can be utilized as biochemical research intermediates for mapping molecular interactions, generating substrate analogs, and supporting structure-activity relationship studies in peptide-based molecular probes.
4. Peptidomimetics And SAR
Fmoc-L-allo-threoninol is applied in peptidomimetic construction where replacing conventional threonine side-chain chemistry with an amino alcohol enables altered conformational behavior and new functional group placement. The protected amino alcohol residue supports iterative peptide analog assembly, while the hydroxymethyl functionality can be transformed into substituents that modulate polarity, steric effects, or hydrogen-bond donor/acceptor patterns relevant to SAR studies. The allo stereocenter provides a stereodefined scaffold for generating analog series that probe the role of side-chain orientation in target recognition. Downstream derivatives prepared from the alcohol functionality can include cyclization precursors and protected intermediates that integrate into larger synthetic schemes for fine chemical synthesis and applied molecular design.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-allo-threoninol is used in process chemistry intermediate preparation for manufacturing routes that require a chiral, Fmoc-protected amino alcohol with orthogonal functional group management. The Fmoc carbamate protects the amine during multi-step synthesis, while the unprotected primary alcohol can be selectively functionalized to create protected intermediates suitable for controlled downstream coupling or purification strategies. The stereochemical integrity associated with the L-allo configuration supports reproducible formation of stereodefined intermediates used in peptide-like active ingredient fragments and related specialty chemical production. The compound's dual functionality enables its incorporation into protected amino acid synthesis sequences that culminate in C- or N-terminal modified building blocks for industrial-scale fine chemical synthesis.
1. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
3. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
4. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
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