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Glu(OtBu)-Val-Cit-PAB-OH

  CAS No.: 2757059-05-3   Cat No.: BADC-01753 4.5  

Glu(OtBu)-Val-Cit-PAB-OH is a non-cleavable ADC linker that has been used to synthesize protein-tubulysin conjugates.

Glu(OtBu)-Val-Cit-PAB-OH

Structure of 2757059-05-3

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ADC Linker
Molecular Formula
C27H44N6O7
Molecular Weight
564.67

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IUPAC Name
tert-butyl (4S)-4-amino-5-[[(2S)-1-[[(2S)-5-(carbamoylamino)-1-[4-(hydroxymethyl)anilino]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoate
Canonical SMILES
CC(C)C(C(=O)NC(CCCNC(=O)N)C(=O)NC1=CC=C(C=C1)CO)NC(=O)C(CCC(=O)OC(C)(C)C)N
InChI
InChI=1S/C27H44N6O7/c1-16(2)22(33-23(36)19(28)12-13-21(35)40-27(3,4)5)25(38)32-20(7-6-14-30-26(29)39)24(37)31-18-10-8-17(15-34)9-11-18/h8-11,16,19-20,22,34H,6-7,12-15,28H2,1-5H3,(H,31,37)(H,32,38)(H,33,36)(H3,29,30,39)/t19-,20-,22-/m0/s1
InChIKey
HPZRSLCEFXXOIR-ONTIZHBOSA-N

Glu(OtBu)-Val-Cit-PAB-OH is a peptide-based compound with significant applications in drug delivery systems, particularly in the design of prodrugs for targeted therapy. The structure includes key components such as glutamic acid (Glu), valine (Val), citrulline (Cit), and para-aminobenzoic acid (PAB), which are designed to optimize the pharmacokinetics and delivery of active pharmaceutical ingredients. The incorporation of an amino acid sequence like this allows for selective cleavage and release of the therapeutic agent at the target site, enhancing the precision of drug delivery and minimizing systemic toxicity. This feature is particularly valuable in cancer treatments, where targeted drug release can help overcome the challenges of conventional chemotherapy.

Another notable application of Glu(OtBu)-Val-Cit-PAB-OH is in the design of antibody-drug conjugates (ADCs) and other biomolecule-based therapeutic agents. The compound serves as a linker or part of a linker-payload system, enabling the attachment of cytotoxic agents to antibodies for targeted drug delivery. The citrulline residue in particular plays an important role in the stability and cleavage of the linker, ensuring the drug is released selectively at the site of action, such as within cancer cells or other diseased tissues. This makes Glu(OtBu)-Val-Cit-PAB-OH an important component in the development of novel ADCs for more effective and localized cancer treatments.

Additionally, Glu(OtBu)-Val-Cit-PAB-OH is being explored in the context of peptide-based vaccines and immunotherapies. The compound’s ability to serve as a flexible linker between immunomodulatory molecules or antigens enhances its utility in designing vaccines with better bioavailability and immune response activation. By strategically incorporating this peptide into vaccine formulations, it may be possible to improve the stability of the antigen, ensure controlled release, and promote a more targeted immune response, which is crucial in the treatment of infectious diseases and cancer immunotherapy.

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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