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Other Specialized Reagents

Cbz-4-Nitro-D-Phenylalanine

Category:

Other Specialized Reagents

CAS NO:

117402-88-7

Standard:

BP,USP,

Price Range:

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Main Sales Markets:

North America,Western Europe,Eastern Europe

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Shanghai Sunwise Chemical Co., Ltd.

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Basic Info

CAS Number

117402-88-7

Pharmacopoeia

BP,USP

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Product Description

Pharmaceutical Raw Materials and Intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

Cbz-4-Nitro-D-Phenylalanine is a specialized chiral building block widely utilized in the field of peptide synthesis and medicinal chemistry. Its chemical structure features a D-phenylalanine backbone protected by a benzyloxycarbonyl (Cbz or Z) group on the amino terminus, with a nitro substituent positioned at the para location of the benzene ring. The molecular formula for this compound is C16H14N2O5, and it is identified by the CAS Registry Number 10387-73-4. This specific stereochemistry, denoted by the "D" configuration, distinguishes it from its more common L-isomer counterpart, making it an essential reagent for synthesizing peptides that require non-natural amino acid residues to enhance metabolic stability or alter biological activity. The primary application of Cbz-4-Nitro-D-Phenylalanine lies in solid-phase peptide synthesis (SPPS) and solution-phase coupling reactions. Researchers frequently employ this derivative to introduce structural diversity into peptidomimetics, which are crucial for developing novel therapeutic agents, including antibiotics, antivirals, and anticancer drugs. The presence of the nitro group serves as a versatile handle for further chemical modifications; it can be readily reduced to an amino group, allowing for the creation of complex heterocyclic systems or the introduction of additional functional groups via diazotization. Furthermore, the Cbz protecting group ensures the amino functionality remains inert during various synthetic steps, only being removed under mild hydrogenation conditions when necessary. Due to its high purity and defined stereochemical integrity, this compound is indispensable for academic research laboratories and pharmaceutical companies engaged in drug discovery campaigns. It facilitates the precise construction of peptide sequences where the spatial arrangement of side chains dictates receptor binding affinity and specificity. Overall, Cbz-4-Nitro-D-Phenylalanine represents a fundamental tool for advancing the synthesis of bioactive molecules with tailored pharmacological profiles.