Alloc-Val-Ala-OH Chemical Properties

Boiling point:

498.3±40.0 °C(Predicted)

Density 

1.155±0.06 g/cm3(Predicted)

pka

3.49±0.10(Predicted)

form 

Solid

InChI

InChI=1S/C12H20N2O5/c1-5-6-19-12(18)14-9(7(2)3)10(15)13-8(4)11(16)17/h5,7-9H,1,6H2,2-4H3,(H,13,15)(H,14,18)(H,16,17)/t8-,9-/m0/s1

InChIKey

LOIWGNGKOQWZSA-IUCAKERBSA-N

SMILES

C(O)(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(OCC=C)=O

Alloc-Val-Ala-OH Usage And Synthesis

Description

Alloc-Val-Ala-OH is a peptide linker with a terminal carboxylic acid group and an Alloc protecting group. The peptide chain can act as a cleavable linker in drug design, such as in antibody drug conjugates (ADC). The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Alloc group is stable to treatment with piperidine and TFA, and can be removed in neutral conditions with catalytic amounts of Pd(PPh3)4 in the presence of PhSiH3. This allows the allyl system to work orthogonality with the most common protecting groups.

Uses

N-Alloc-L-valyl-L-alanine is a building block in the synthesis of Tesirine, a clinical antibody-drug conjugate pyrrolobenzodiazepine dimer payload.