3-MPA(Trt)

3-MPA(Trt) is a trityl-protected amino acid derivative in which the side-chain functionality is present as 3-MPA (3-mercapto-propylamine) functionality while the amino group is protected by a trityl (Trt) group. The molecule contains both an amino functionality masked as a trityl carbocation-stabilized protecting group and a carboxyl group, with the trityl protection serving to suppress undesired side reactions during stepwise coupling while the sulfur-containing side chain provides a polarizable thiol handle upon deprotection. In peptide chemistry and chemical biology workflows, it is used as a protected building block or intermediate for assembling modified peptides and for introducing sulfur-bearing functionality into amino acid sequences for labeling, conjugation, or structure-activity studies.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25694

CAS No:27144-18-9

Synonyms/Alias:27144-18-9;3-(tritylthio)propanoicacid;3-(Tritylthio)propionicacid;S-Trityl-3-mercaptopropionicacid;3-Tritylsulfanylpropionicacid;3-(tritylmercapto)propionicacid;3-(tritylsulfanyl)propanoicacid;3-[(triphenylmethyl)sulfanyl]propanoicacid;ST50997125;mpa(trt)-oh;NSC96707;PubChem12845;ACMC-1CMZ4;AC1Q5WG6;SCHEMBL34785;3-tritylsulfanylpropanoicacid;KSC489O4P;3-Tritylmercapto-Propionicacid;53695_ALDRICH;3-tritylmercaptopropionicacid;3-tritylsulfanyl-propionicacid;CHEMBL409296;53695_FLUKA;BDBM23806;C22H20O2S

Chemical Name:S-Trityl-3-mercaptopropionic acid

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M.F/Formula
C22H20O2S
M.W/Mr.
348,46 g/mole

3-MPA(Trt) is a Trt-protected 3-mercapto propylamine derivative used as a sulfur-containing amino acid building block in peptide and chemical synthesis workflows. The presence of a thioether-protected thiol (Trt-protected) provides controlled handling of the reactive sulfur functionality during coupling and intermediate assembly, while the amino functionality supports downstream formation of amide and related linkages. This reagent is commonly selected when protecting-group stability during peptide assembly is required and when the sulfur-containing side chain must be introduced as a defined, late-stage functional motif.

1. Sulfur-Containing Peptide Building

3-MPA(Trt) is used by peptide synthesis groups to incorporate a protected mercapto-propyl side chain motif into custom peptides and peptide fragments. Researchers favor this protected format to maintain thiol compatibility during stepwise assembly, especially when multi-step coupling sequences require reliable chemoselectivity. The Trt protection strategy helps keep the sulfur functionality from interfering with coupling conditions, enabling consistent construction of thioether/thio-functionalized peptide targets that are later processed to reveal the reactive handle as needed for further derivatization.

2. Bioconjugation Linker Precursors

3-MPA(Trt) supports chemical biology and bioconjugation workflows where a controlled, sulfur-bearing functional group is required to generate site-specific conjugation reagents. Teams developing peptide-protein conjugates, affinity reagents, or modular linker systems use this type of protected thiol precursor to defer thiol reactivity until after the conjugation scaffold is assembled. By providing a defined protected sulfur functionality, the reagent helps streamline downstream coupling and labeling steps while reducing premature side reactions that can occur with free thiols.

3. Pharmaceutical Intermediate Synthesis

3-MPA(Trt) is also used in medicinal chemistry and pharmaceutical intermediate development as a protected sulfur-containing amino building block for constructing thio-functional fragments. Process and R&D chemists commonly select this reagent when the sulfur functionality must be introduced in a controlled manner during intermediate elaboration, while the amino group enables formation of amide and related connectivity patterns. The Trt-protected thiol form provides a practical handle for sequencing synthesis steps so that the reactive sulfur can be unmasked or transformed at the appropriate stage of the route.

4. Thio-Functional Material Modifications

3-MPA(Trt) finds use in biomaterials and surface functionalization development where sulfur-containing linkers are required to attach organic components to polymers, nanoparticles, or other material surfaces. Materials scientists and chemical engineers often use protected thiol precursors to manage reactivity during material processing, then convert to a reactive thiol (or thiol-derived functionality) for subsequent immobilization or crosslinking chemistry. This workflow benefit is particularly relevant when the material fabrication process involves multiple steps that would otherwise be sensitive to free thiol oxidation or uncontrolled coupling.

Size
25 g;100 g;500 g;1 kg;
InChI
1S/C22H20O2S/c23-21(24)16-17-25-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2,(H,23,24)
InChI Key
AECGEIVNZGQBJT-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCCC(=O)O

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