Z-dehydroalanine
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Z-dehydroalanine

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Category
CBZ-Amino Acids
Catalog number
BAT-005755
CAS number
39692-63-2
Molecular Formula
C11H11NO4
Molecular Weight
221.21
Z-dehydroalanine
IUPAC Name
2-(phenylmethoxycarbonylamino)prop-2-enoic acid
Synonyms
Z-dehydro-Ala-OH
Purity
99%
Storage
Store at 2-8°C
InChI
InChI=1S/C11H11NO4/c1-8(10(13)14)12-11(15)16-7-9-5-3-2-4-6-9/h2-6H,1,7H2,(H,12,15)(H,13,14)
InChI Key
QCHJVTWVRPQBBU-UHFFFAOYSA-N
Canonical SMILES
C=C(C(=O)O)NC(=O)OCC1=CC=CC=C1

Z-dehydroalanine, an unconventional amino acid boasting distinctive chemical characteristics, finds a multitude of applications across scientific and industrial domains. Here are four key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Integral to the synthesis of modified peptides and proteins, Z-dehydroalanine leverages its reactive double bond to create cross-links with other amino acids. This unique property results in the production of peptides endowed with heightened stability and activity positioning Z-dehydroalanine as a pivotal building block in the development of innovative therapeutic peptides and cutting-edge research tools.

Enzyme Mechanism Studies: Delving into the intricate world of enzyme mechanisms, researchers utilize Z-dehydroalanine to investigate the intricacies of dehydratases and lyases. By virtue of the αβ-unsaturated system present in Z-dehydroalanine, scientists can mimic transitional states and reaction intermediates offering valuable insights into enzyme active sites and catalytic processes. This application serves as a stepping stone towards unraveling enzyme functions and crafting precise enzyme inhibitors.

Protein Modification: Enabling targeted chemical modifications within proteins, Z-dehydroalanine can be seamlessly incorporated to act as a site for attaching diverse chemical groups such as fluorophores affinity tags or drug moieties. This functional feature facilitates the exploration of protein dynamics interactions and localization within complex biological systems opening doors to a deeper understanding of protein behavior and function.

Material Science: In the realm of material science, the exceptional properties of Z-dehydroalanine come to the fore in the realm of advanced biomaterials. Functioning as a vital cross-linker in the production of hydrogels and other polymeric materials, Z-dehydroalanine imparts mechanical strength and versatile functionality to these materials. The resulting biomaterials exhibit promising applications in domains such as drug delivery tissue engineering and biosensors showcasing the diverse and impactful role of Z-dehydroalanine in cutting-edge material science advancements.

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