N-(Benzyloxycarbonyloxy)succinimide
[CAS# 13139-17-8]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: N-(Benzyloxycarbonyloxy)succinimide
• Synonyms: Benzyl succinimido carbonate; Z-ONSu; Z-OSu; Cbz-Cl; N-Benzyloxycarbonyloxy succinimide
• Molecular Formula: C₁₂H₁₁NO₅
• Molecular Weight: 249.22
• CAS Registry Number: 13139-17-8
• EC Number: 236-075-3
• SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2=CC=CC=C2

Properties

• Melting point: 80-82 °C (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N-(Benzyloxycarbonyloxy)succinimide, commonly known as BOC-NHS, is a chemical compound used predominantly in organic synthesis and peptide chemistry. It combines the succinimide ring with a benzyloxycarbonyl group, making it a useful reagent in various chemical transformations.

The discovery of N-(Benzyloxycarbonyloxy)succinimide is rooted in the development of protecting groups for amines and carboxylic acids, a crucial aspect of organic synthesis. The benzyloxycarbonyl (BOC) group was introduced to offer a stable and easily removable protecting group for amino groups in peptide synthesis. Researchers found that incorporating the NHS ester functionality into the BOC group provided additional versatility. The resulting compound, BOC-NHS, is known for its ability to selectively activate carboxylic acids for coupling reactions while protecting the amino groups, thereby facilitating the synthesis of complex peptide sequences.

In practical applications, N-(Benzyloxycarbonyloxy)succinimide serves as a coupling reagent in peptide synthesis. It is used to convert carboxylic acids into active esters, which can then react with amines to form peptide bonds. This process is essential in the production of peptides and proteins for research and pharmaceutical applications. The stability of the BOC group under various reaction conditions and its ease of removal are significant advantages, making BOC-NHS a preferred reagent for many synthetic chemists.

Another important application of BOC-NHS is in the synthesis of peptide derivatives and complex organic molecules. Its ability to protect functional groups while allowing for selective reactions enhances its utility in designing and constructing intricate chemical structures. The compound's role in facilitating the formation of peptide bonds and its compatibility with a wide range of reaction conditions make it a valuable tool in organic chemistry and drug development.

Researchers continue to explore new uses for N-(Benzyloxycarbonyloxy)succinimide, particularly in the development of novel peptide-based therapeutics and materials. Its versatility and effectiveness as a coupling reagent and protecting group underscore its importance in advancing the field of organic synthesis.

Overall, N-(Benzyloxycarbonyloxy)succinimide represents a significant advancement in synthetic chemistry. Its discovery and applications highlight its role in facilitating peptide synthesis and constructing complex organic molecules.

References

2008. Benzyl 2,5-dioxopyrrolidin-1-yl carbonate. Acta Crystallographica. Section E, Structure Reports Online, 64(7).
DOI: 10.1107/s1600536808015948

2019. Recent advances in the chemical synthesis and semi-synthesis of poly-ubiquitin-based proteins and probes. Science China Chemistry, 62(3).
DOI: 10.1007/s11426-018-9401-8

2005. α-Amino Protection. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-021-00695