Z-Ala-OH

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Cat Number

PIPB-0737

CAS Number

1142-20-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

1142-20-7

EINECS

214-532-8

Synonyms

N-Carbobenzyloxy-L-alanine; Z-L-Alanine N-[(Benzyloxy)carbonyl]-L-alanine

Molecular Formula

C11H13NO4

Molecular Weight

223.22

Smiles

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

Appearance

White to off-white crystalline powder

Melting Point

80-90℃

Boiling Point

364.51℃

Relative Density

1.24

pKa

General Description

Z-Ala-OH is a highly pure amino acid derivative and a versatile building block for use in organic synthesis and peptide chemistry. It contains a stable benzyloxycarbonyl protecting group on the amino group of L-alanine, a chemical property that maintains the structure's stability during complex chemical reactions.

Application

Z-Ala-OH is commonly used in solid-phase and liquid-phase peptide synthesis to produce pharmaceutical peptides and biochemical reagents. It is used as a monomer or intermediate in specialized laboratory research and the large-scale production of bioactive peptide chains.

Z-Ala-OH is photochemically activated through halogen-bonded complexes (XBCs) formed between CBr₄ and various tertiary amines (DMAP or DABCO being optimal). Under 370 nm LED or sunlight irradiation, the XBC generates an N-brominated amine, iminium ion and hemiaminal ester intermediates (detected by DI-HRMS). Subsequent nucleophilic attack by H-Phe-OMe furnishes the corresponding Z-Ala-Phe-OMe dipeptide in upto 79% isolated yield.

Fig. 1 Photochemical coupling of Z-Ala-OH. (Routsi E A.; et al. 2024)

References

Routsi E A, et al. Computational and Spectroscopic Studies on the Formation of Halogen-Bonded Complexes Between Tertiary Amines and CBr4 and Application in the Light-Mediated Amino Acid Coupling. ChemPlusChem, 2024, 89(9): e202400019.

In which research fields is Z-Ala-OH commonly used?

It is essential for peptide drug discovery, biochemical research, and pharmaceutical development.

What is the purity specification for your Z-Ala-OH?

We typically supply high-purity grades suitable for sensitive synthesis applications.

Do you offer Z-Ala-OH in bulk quantities?

Yes, we supply Z-Ala-OH from lab-scale to commercial bulk quantities.