Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH is an Fmoc-protected amino acid building block bearing an isoleucine residue linked to a threonine-derived side chain modified with a Psi(Me,Me)pro moiety, classifying it as a protected, structurally constrained amino acid derivative for peptide assembly. The molecule contains a free carboxylic acid and an Fmoc carbamate-protected amino group, while the threonine hydroxyl is incorporated into the Psi(Me,Me)pro substituent that constrains side-chain geometry and provides a sterically defined functional element for structure-activity studies. In peptide synthesis workflows, it functions as a residue-level precursor that can be incorporated into protected peptide chains to introduce the Psi(Me,Me)pro-constrained threonine motif, supporting the preparation of analog peptides for conformational analysis and chemical biology investigations.
CAT No: CP27609
CAS No:957780-52-8
Synonyms/Alias:957780-52-8;Fmoc-Ile-Thr(Psime,Mepro)-OH;Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH;Fmoc-Ile-Thr[Psi(Me,Me)Pro]-OH;MFCD18427359;Fmoc-L-Ile-L-Thr(Psi(Me,Me)pro)-OH;Fmoc-L-Ile-L-Thr[PSI(Me,Me)Pro]-OH;(4S,5R)-3-[(2S,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carboxylic acid;Fmoc-Ile-Thr(Psi(Me ,Me)pro)-OH;AKOS025289509;AS-60160;DA-63530;FF111334;(4S,5R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)-L-isoleucyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid;(4S,5R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)-L-isoleucyl)-2,2,5-trimethyloxazolidine-4-carboxylicacid;(4S,5R)-3-(N-(9-Fluorenylmethyloxycarbonyl)-L-isoleucinyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid;
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH is an Fmoc-protected amino acid derivative in which the side chain of threonine is converted to a constrained Psi(Me,Me)pro motif, generating a stereochemically defined, peptidomimetic-like handle for peptide backbone mimicry. The molecule contains an N-terminal Fmoc carbamate that supports standard base-mediated removal during solid-phase peptide synthesis, while the C-terminal carboxylic acid remains available for amide bond formation and subsequent coupling chemistries. The Psi(Me,Me)pro substitution pattern introduces bulky, geminally substituted character that can influence conformational preferences and protease resistance in peptide analogs. The presence of a chiral amino acid core (Ile/Thr-derived stereocenters) and the protected side-chain architecture makes the compound suitable as a chiral building block and downstream intermediate for chemically defined structure-activity relationship studies and synthetic methodology development.
1. Peptide Synthesis
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH supports peptide building block preparation for automated and manual peptide assembly by combining an Fmoc-protected nitrogen with a free carboxylic acid for reliable peptide coupling. The threonine-derived Psi(Me,Me)pro side-chain architecture can be carried through coupling steps without requiring side-chain functional group manipulation, enabling consistent incorporation of a constrained residue into peptide sequences. The chiral centers embedded in the Ile/Thr framework provide stereodefined monomer identity, which is critical for generating sequence-specific analog libraries. The resulting peptide products can be used to probe backbone-recognition effects and to generate peptidomimetic scaffolds with controlled local geometry.
2. Peptidomimetics SAR Studies
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH serves in peptidomimetic and SAR studies where conformational restriction at the threonine position is used to modulate binding-site interactions. The Psi(Me,Me)pro motif, bearing Me substituents, introduces steric and stereoelectronic features that can alter hydrogen-bonding patterns and side-chain orientation compared with native threonine. The Fmoc-protected amino acid format enables systematic placement of this constrained residue within longer analogs, supporting structure-activity relationship workflows based on defined stereochemistry and side-chain topology. Downstream peptide analogs generated from this monomer can be applied as chemical probes for studying molecular recognition and for mapping residue-level contributions in bioactive sequence designs.
3. Protected Amino Acid Chemistry
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH functions as a protected amino acid chemistry intermediate by pairing an Fmoc carbamate with a side-chain-modified threonine residue that is already pre-organized for peptide incorporation. The N-Fmoc group provides orthogonal protection relative to typical side-chain chemistries, allowing deprotection under standard base conditions during synthesis while maintaining the integrity of the Psi(Me,Me)pro motif. The free C-terminal carboxylic acid enables conversion into activated esters or direct coupling partners, supporting controlled amide bond formation in both solution-phase and solid-phase strategies. The stereodefined chiral amino acid core further supports reproducible downstream transformations when preparing defined peptide fragments, fragment libraries, and synthetic intermediates for fine chemical production.
4. Chemical Biology Probes
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH can be employed in chemical biology research to generate peptide-based probes that interrogate protein-ligand interactions with residue-level precision. The constrained Psi(Me,Me)pro side chain can mimic elements of threonine-like functionality while reducing conformational freedom, which may influence recognition by enzymes or binding domains in a way that is attributable to structure rather than heterogeneous side-chain dynamics. The Fmoc-enabled synthesis route supports incorporation into longer probe constructs that include additional functional residues for affinity tags, reporter incorporation, or modular fragment assembly. The resulting labeled or functionalized peptide probes can be used to support mechanistic studies and to generate chemically defined reagents for biochemical investigation.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH is suitable for pharmaceutical manufacturing workflows that require controlled, stereodefined protected amino acid inputs for peptide intermediate preparation. The Fmoc-protected nitrogen and carboxylic acid functionality align with common peptide synthesis manufacturing strategies, where orthogonal protection and predictable coupling behavior are required for scalable production of peptide intermediates. The side-chain Psi(Me,Me)pro motif can be carried through manufacturing steps as a stable, pre-installed structural element, reducing the need for late-stage side-chain remodeling that can introduce variability. The compound therefore functions as a chiral process chemistry intermediate for producing well-defined peptide building blocks and peptidomimetic fragments used in downstream manufacturing of peptide-based candidates and related research materials.
6. Side-Chain Functionalization Platforms
Fmoc-Ile-Thr(Psi(Me,Me)pro)-OH provides a platform for side-chain functionalization strategies where the threonine position is pre-engineered into a constrained Psi(Me,Me)pro group. The bulky Me-substituted motif can serve as a steric and stereochemical determinant during peptide assembly, enabling subsequent derivatization of neighboring residues without disturbing the pre-installed side-chain geometry. The Fmoc-protected amino acid format supports iterative sequence construction, after which the synthesized peptide fragments can be further modified through orthogonal chemistries at other functional handles present in the sequence design. The resulting functionalized peptide scaffolds can be employed in synthetic organic chemistry and applied peptide science to generate defined analogs for binding studies, enzyme substrate mapping, and molecular design campaigns.
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