13139-17-8

N-CBZ-Succinamide 13139-17-8

Physical properties:

N-(Benzyloxycarbonyloxy)succinimide (CAS 13139-17-8), also known as Z-ONSu or Cbz-OSU, is a white to off-white solid (𝐶12𝐻11𝑁𝑂5) with a melting point of 80-82∘C. Primarily used as a peptide reagent for introducing the benzyloxycarbonyl (Cbz/Z) protecting group onto amino groups, it is valued for its stability, high reactivity, and moisture sensitivity.

Key Properties and Specifications:

  • Appearance: White to off-white crystalline powder.
  • Molecular Weight: 249.22g/mol.
  • Melting Point: 80-82∘C (lit.).
  • Solubility: Sparingly soluble in water.
  • Assay: Typically ≥98%.
  • Stability: Moisture-sensitive; requires storage under inert gas and at low temperatures (typically 2-8∘C or <15∘C)

Main Applications:

  • Peptide Synthesis: It selectively introduces the Z-amino protecting group to amino acids, amino-glycosides, and aminoglycoside antibiotics.
  • Reagent for Organic Synthesis: Acts as a reagent to create, for example, N-protected amino acids

 

Category: Tags: ,

Safety and Handling:

  • Hazard Identification: Causes skin irritation, serious eye irritation, and may cause respiratory irritation.
  • Handling: Wear suitable protective clothing and avoid breathing dust,

N-(Benzyloxycarbonyloxy)succinimide (CAS 13139-17-8), Is a key peptide synthesis reagent, commonly known as Cbz-OSu or Z-OSu. It is used to introduce the carboxybenzyl (Cbz/Z) protecting group. Key synonyms include Benzyl N-succinimidyl carbonate, O-Cbz-N-hydroxysuccinimide, and N-Carbobenzoxyoxysuccinimide.

Main Synonyms and Chemical Names for 13139-17-8:

  • N-(Benzyloxycarbonyloxy)succinimide (Most common)
  • Cbz-OSu / Z-OSu
  • Benzyl N-succinimidyl carbonate
  • O-Cbz-N-hydroxysuccinimide
  • N-Carbobenzoxyoxysuccinimide
  • N-Benzyloxycarbonyloxysuccinimide
  • Benzyl (2,5-dioxopyrrolidin-1-yl) carbonate
  • O-Benzyloxycarbonyl-N-hydroxysuccinimide
  • 1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione
  • Z-ONSu

The compound is typically used in peptide synthesis to protect amino groups from unwanted reactions.

N-(Benzyloxycarbonyloxy)succinimide (CAS 13139-17-8), often referred to as

is a widely used reagent in organic synthesis, particularly in medicinal chemistry and biochemistry. Its primary function is as a selective, stable, and convenient reagent for the introduction of the benzyloxycarbonyl (Cbz or Z) protecting group to amino groups (𝑁𝐻2).

Uses and Applications:

  • Peptide Synthesis: Cbz-OSu is commonly used to protect amino acid residues during peptide chain elongation. It ensures that the amine group does not interfere with the coupling reaction, allowing for selective reactions, and is known for its stability under various conditions.
  • Amino Protection in Organic Synthesis: It serves as a reagent for the selective Cbz-protection of amines, often used as a safer or more convenient alternative to benzyl chloroformate.
  • Preparation of Peptide Thioacids: It is employed in the preparation of peptide thioacids, which are used as peptide precursors.
  • Aminoglycoside Derivatives Preparation: The compound is used in the synthesis of aminoglycoside derivatives, which are crucial for studying topoisomerase inhibition in both human and bacterial cells.
  • Specific Chemical Synthesis: It is involved in the synthesis of specialized molecules, including:
    • Enantiomers of cyclic methionine analogs (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acid.
    • 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.
    • Total synthesis of complex molecules like (-)-diazonamide A and (-)-sanglifehrin A.
  • N-Trans Diprotection of Cyclen: It is used in the regioselective N-trans diprotection of cyclen.

 

FAQs

What is N-CBZ-Succinamide?
N-CBZ-Succinamide is an organic compound commonly used as an intermediate in pharmaceutical synthesis and peptide chemistry.
What is the CAS number of N-CBZ-Succinamide?

The CAS number is 13139-17-8, which uniquely identifies this compound.

What are the main uses of N-CBZ-Succinamide?
It is primarily used in pharmaceutical manufacturing, peptide synthesis, and organic research.
What is the molecular formula of N-CBZ-Succinamide?

The molecular formula is C₁₂H₁₃NO₅.

Is N-CBZ-Succinamide safe to handle?
It should be handled using proper safety precautions such as gloves, protective clothing, and working in a well-ventilated area.
How should N-CBZ-Succinamide be stored?
Store in a cool, dry place in tightly sealed containers, away from moisture and direct sunlight.

Related products