Z-VAL-ALA-OH

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Cat Number

INT24787891

CAS Number

24787-89-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

24787-89-1

Storage

2-8℃

Synonyms

Z-L-VALYL-L-ALANINE

Molecular Formula

C16H22N2O5

Molecular Weight

322.36

Smiles

C[C@@H](C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1

Appearance

White to off-white solid

Melting Point

165℃

Boiling Point

575.5℃

Relative Density

1.2

pKa

3.49

General Description

Z-VAL-ALA-OH is a protected dipeptide composed of L-valine and L-alanine. It is a pre-formed sequence used to simplify the synthesis of larger peptides.

Mechanism of Action

It acts as a fragment building block. By incorporating a pre-synthesized dipeptide, the number of coupling steps in a sequence is reduced, which can improve overall yield and reduce purification complexity.

Application

It is commonly used in the synthesis of peptide-based enzyme substrates and inhibitors, specifically targeting proteases.

TAK-500 is a first-in-class antibody-drug conjugate (ADC) that delivers the STING agonist dazostinag selectively to CCR2 immune cells for immuno-oncology applications. The key challenge was conjugating the cyclic dinucleotide (CDN) payload, which lacks conventional conjugation handles and is highly hydrophilic.
The authors introduced a self-immolative spacer between the adenine and the Z-Val-Ala-OH-derived cathepsin B-cleavable dipeptide. This design ensured plasma stability while enabling rapid payload release upon lysosomal internalization. The optimized linker-payload 9 was conjugated stochastically to a CCR2-targeting antibody via cysteine maleimide chemistry, yielding TAK-500 with an average drug-to-antibody ratio (DAR) of 4.

Fig. 1 Self-immolation of spacers attached to the Nitrogen on the Nucleobase. (Lee H M.; et al. 2025)

References

Lee H M, et al. Identification of a Novel Linker Enabling the Bioconjugation of a Cyclic Dinucleotide for the STING Antibody-Drug Conjugate TAK-500. Bioconjugate Chemistry, 2025, 36(11): 2423-2435.