α-carbobenzoxy-L-isoleucine p-nitrophenyl ester, CAS No. 2130-99-6

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2130-99-6

Catalog No. EBD2208256

CAS 2130-99-6

Name α-carbobenzoxy-L-isoleucine p-nitrophenyl ester

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Basic Information

Synonyms: p-Nitrophenyl-N-benzyloxycarbonyl-L-isoleucinat α-carbobenzoxy-L-isoleucinep-nitrophenylester benzyloxycarbonyl-l-isoleucine4-nitrophenylester benzloxycarbonyl-l-isoleucinep-nitrophenylester n-cbz-l-isoleucinep-nitrophenylester n-carbobenzoxy-l-isoleucine-p-nitrophenylester z-ile-onp z-isoleucine-onp z-l-isoleucine4-nitrophenylester z-l-isoleucinep-nitrophenylester N-CBZ-L-Isoleucinep-nitrophenylesterN-Carbobenzyloxy-L-isoleucinep-nitrophenylester 4-nitrophenylN-[(benzyloxy)carbonyl]isoleucinate 4-nitrophenylN-[(benzyloxy)carbonyl]-L-isoleucinate

Molecular Formula: C20H22N2O6

Molecular Weight: 386.4

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters

Product Description:

N-Carbobenzoxy-L-isoleucine 4-nitrophenyl ester is a protected amino acid active ester derivative. It features an L-isoleucine backbone where the α-amino group is protected by a benzyloxycarbonyl (Cbz or Z) group, and the carboxylic acid is activated as a 4-nitrophenyl ester. This molecular design makes it a reactive acylating agent, particularly useful in peptide synthesis. The primary application of this compound is as a specialized building block in solid-phase and solution-phase peptide synthesis. The Cbz protecting group is stable under acidic conditions but can be readily removed by catalytic hydrogenation or hydrogenolysis. The 4-nitrophenyl ester moiety serves as an excellent leaving group, facilitating efficient amide bond formation with the amino group of another amino acid or peptide fragment under mild conditions, minimizing racemization. It is specifically employed for the controlled incorporation of the hydrophobic L-isoleucine residue into peptide chains. As a protected and activated amino acid derivative, it is a crucial reagent in the research and development of therapeutic peptides, peptidomimetics, and other bioactive molecules. Handling requires standard precautions for laboratory chemicals, and it should be stored under inert conditions to maintain stability.

Physical Properties

Boiling Point: 561.3°Cat760mmHg

Flash Point: 293.2°C

Density: 1.239g/cm3