Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH is a protected, side-chain-modified amino acid derivative featuring an Fmoc-protected lysine core bearing a Boc-protected amino substituent and a threonine side-chain incorporated as a Psi(Me,Me)pro-modified unit. The molecule contains an Fmoc carbamate on the lysine α-amino group, a Boc-protected lysine ε-amino group, and a carboxylic acid at the C-terminus, while the Thr(Psi(Me,Me)pro) portion introduces a constrained, Psi-substituted proline-like functionality that can present steric and conformational bias relative to unmodified threonine. As a multi-protected amino acid building block, it is employed in stepwise peptide synthesis and related structure-activity or chemical biology studies where controlled chemoselectivity and incorporation of a conformationally restricted threonine analogue are required.
CAT No: CP27583
CAS No:911838-56-7
Synonyms/Alias:911838-56-7;Fmoc-Lys(Boc)-Thr{psi(Me,Me)pro}-OH;Fmoc-Lys(Boc)-Thr[Psi(Me,Me)Pro]-OH;C33H43N3O8;6954AH;Fmoc-Lys(Boc)-Thr(Psime,Mepro)-OH;AKOS025289503;ZINC169722876;CF-1366;AK170268;(4S,5R)-3-(Fmoc-Lys(Boc))-2,2,5-trimethyl-oxazolidine-4-carboxylicacid
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH is a protected lysine-threonine amino acid derivative designed for stepwise peptide assembly, bearing an Fmoc group on the lysine alpha-amino functionality and a Boc-protected side-chain amine on the lysine residue. The threonine side chain is incorporated as a Psi(Me,Me)pro-configured protected hydroxyl-bearing motif, creating a constrained, stereodefined handle that can be carried through coupling steps while modulating reactivity relative to unprotected alcohols. The molecule contains a free C-terminal carboxylic acid for amide bond formation, while the multiple protecting groups (Fmoc, Boc, and the Psi(Me,Me)pro hydroxyl protection strategy) support orthogonal deprotection logic and predictable chemoselectivity. The presence of stereogenic centers on lysine and threonine enables stereochemically controlled incorporation into peptides and peptidomimetic scaffolds, with downstream utility as a protected intermediate for functional group unveiling and further derivatization.
1. Peptide Synthesis
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH supports solid-phase or solution-phase peptide synthesis where lysine provides an orthogonally protected side-chain amine and threonine contributes a protected hydroxyl suitable for controlled deprotection. The Fmoc group enables standard base-labile N-terminal activation, while the Boc group on the lysine side chain can be removed under acid conditions to reveal an amine for subsequent coupling or conjugation. The Psi(Me,Me)pro-protected threonine hydroxyl can be maintained during peptide chain elongation to prevent side reactions, then unveiled later to enable phosphorylation-mimicking chemistry, glycomimetic elaboration, or selective functionalization. The free carboxylic acid at the C-terminus participates in peptide coupling chemistry, allowing incorporation as a lysine-linked threonine building block for peptide building block preparation and controlled side-chain patterning in sequence-defined constructs.
2. Side-Chain Functionalization
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH is suitable for side-chain functionalization workflows that require orthogonal protection of both amine and hydroxyl functionalities within a single chiral intermediate. The lysine Boc-protected amine can be selectively deprotected to introduce nucleophilic reactivity for amide formation, carbamate formation, or attachment of solubilizing tags, while the threonine protected hydroxyl remains masked to avoid competing reactions during early derivatization steps. The Psi(Me,Me)pro protection strategy can be leveraged to tune alcohol reactivity, enabling later conversion into functional groups relevant to biochemical mimicry such as phospho-serine/phospho-threonine analogs or other oxygen-based substituents. The resulting derivatives can be used to generate structured amino acid modification libraries, peptidomimetic scaffolds, and sequence-context-dependent functional analogs for downstream synthetic and analytical studies.
3. Chemical Biology Conjugation
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH aligns with chemical biology and biomolecule labeling efforts that rely on controlled presentation of reactive handles for bioconjugation chemistry. The orthogonally protected lysine side-chain amine enables stepwise conjugation strategies where amine unveiling can be timed after peptide assembly, reducing the likelihood of premature crosslinking. The threonine hydroxyl protection supports retention of an oxygen-functional site for later transformation into conjugation-ready motifs, including linker installation or formation of oxygen-bearing bioorthogonal intermediates depending on the chosen downstream chemistry. The stereodefined amino acid backbone helps maintain structure-function relationships in labeled peptides, facilitating the generation of defined conjugates for receptor-binding probes, enzyme substrate analogs, and mechanistic studies that depend on precise spatial arrangement of functional groups.
4. Peptidomimetics And SAR Studies
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH can be applied to peptidomimetic construction and structure-activity relationship studies where protected amino acid derivatives are needed to systematically vary side-chain chemistry while preserving backbone stereochemistry. The lysine residue with Fmoc/Boc protection supports sequential assembly into constrained scaffolds, while the Psi(Me,Me)pro-protected threonine hydroxyl provides a controllable functional element that can be converted into alternative substituents for SAR mapping. The defined stereocenters on both the lysine and threonine components help maintain consistent three-dimensional geometry across analog series, which is critical when comparing binding or recognition trends in SAR studies. The C-terminal carboxylic acid supports coupling to diverse fragments, enabling rapid synthesis of analog panels and enabling downstream analytical characterization of structure-dependent properties in amino acid chemistry and peptide science.
5. Pharmaceutical Intermediate Preparation
Fmoc-Lys(Boc)-Thr(Psi(Me,Me)pro)-OH serves as a protected amino acid intermediate for manufacturing-oriented peptide intermediate preparation where orthogonality and chemoselective deprotection are required for scalable routes. The Fmoc group provides a robust N-protection handle compatible with standard peptide coupling sequences, while the Boc side-chain amine protection supports controlled release of nucleophilicity for subsequent functionalization steps in intermediate workflows. The Psi(Me,Me)pro protection on the threonine hydroxyl can be used to manage reactivity during multi-step synthesis, helping prevent undesired side reactions that can complicate purification and downstream conversion. The resulting intermediate can be carried into further derivatization to generate defined peptide building blocks and functionalized amino acid derivatives used in fine chemical synthesis and pharmaceutical intermediate production, supporting consistent stereochemical outcomes across batch manufacture.
1. Myotropic activity of allatostatins in tenebrionid beetles
2. TMEM16F and dynamins control expansive plasma membrane reservoirs
3. 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