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Fmoc-(D-Phe)-OSu

  CAS No.: 182410-73-7   Cat No.: BADC-01701 4.5  

Fmoc-(D-Phe)-OSu is a Fmoc-protected D-phenylalanine ADC linker intermediate with N-hydroxysuccinimide ester, supporting efficient conjugation and controlled payload attachment in antibody-drug conjugates. Keywords: ADC linker, Fmoc protection, NHS ester, D-phenylalanine linker, payload conjugation.

Fmoc-(D-Phe)-OSu

Structure of 182410-73-7

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ADC Linker
Molecular Formula
C28H24N2O6
Molecular Weight
484.50

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IUPAC Name
(2,5-dioxopyrrolidin-1-yl) (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoate
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)C(CC2=CC=CC=C2)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
InChI
InChI=1S/C28H24N2O6/c31-25-14-15-26(32)30(25)36-27(33)24(16-18-8-2-1-3-9-18)29-28(34)35-17-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,29,34)/t24-/m1/s1
InChIKey
VLXHZQQUTCVLGU-XMMPIXPASA-N

Fmoc-(D-Phe)-OSu, also known as Fluorenylmethoxycarbonyl-D-Phenylalanine-OSu, is a versatile chemical reagent commonly employed in peptide synthesis. Here are four key applications of Fmoc-(D-Phe)-OSu:

Solid-Phase Peptide Synthesis (SPPS): Central to SPPS, Fmoc-(D-Phe)-OSu plays a pivotal role in incorporating D-Phenylalanine residues into peptides. Its affinity for amine groups facilitates efficient coupling, a critical step in crafting peptides with intricate sequences. This methodology lies at the core of peptide generation for diverse research and therapeutic endeavors.

Protease Inhibition Studies: Peptides featuring D-Phenylalanine are instrumental in exploring protease inhibition mechanisms. Fmoc-(D-Phe)-OSu enables the synthesis of these peptides, which act as potent competitive protease inhibitors. Delving into protease interactions aids in formulating novel therapeutic agents for diseases marked by protease aberrations, pushing the boundaries of medical advancement.

Drug Development: Within the pharmaceutical sphere, Fmoc-(D-Phe)-OSu serves as a cornerstone in synthesizing peptide-based drugs. By incorporating D-amino acids like D-Phenylalanine, peptide stability against enzymatic breakdown is bolstered, enhancing the pharmacokinetic attributes of these drugs. This enhancement propels peptide drugs to higher efficacy levels for clinical utility, fostering improved treatment outcomes.

Peptide-Based Diagnostics: In the realm of diagnostics, Fmoc-(D-Phe)-OSu finds application in crafting peptide-based diagnostic tools. Synthetic peptides featuring D-Phenylalanine residues are harnessed in assays and biosensors to detect specific biomolecules. These diagnostic tools play a vital role in early disease detection and monitoring treatment responses, underscoring their significance in healthcare management.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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Historical Records: Boc-Gly-Gly-Phe-Gly-OH (TFA) | diMal-O-CH2COOH | Isofistularin-3 | Propargyl-O-C1-amido-PEG2-C2-NHS ester | Mal-PEG4-Val-Cit-PAB-OH | Mal-PEG1-Val-Cit-PABC-OH | MPB-MMAF | D8-MMAF hydrochloride | Fmoc-(D-Phe)-OSu
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