(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate - ≥96% , CAS No.1426827-79-3

CAS: 1426827-79-3 Cat. No.: R485474 Molecular Weight: 291.3 EC Number: 878-791-4

GRADE & PURITY ≥96%

Synonyms

BCN-NHS | BCN-CO-NHS

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Application

227,228,229

Overview

Description

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethylN-succinimidyl carbonate may be used to functionalize the primary amines of the lysine residue of recombinant elastin-like proteins (ELPs). These functionalized ELPs quickly undergo cross-linking via bio-orthogonal strain-promoted azide-alkyne cycloaddition reactions to form hydrogels with high gelation kinetics and tunable mechanics, making them useful biomaterials for cell encapsulation.{67It may also be used to synthesize bicyclononyne functionalized poly(ethylene glycol) polymer coatings with anti-fouling properties towards protein adhesion and cell adhesion for supramolecular ureidopyrimidinone (UPy) based materials.Succinimidyl ester/NHS functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.

Specifications

Synonyms

BCN-NHS | BCN-CO-NHS

Specifications & Purity

≥96%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥96%

Names and Identifiers

• Canonical Smiles: C1CC2C(C2COC(=O)ON3C(=O)CCC3=O)CCC#C1
• IUPAC Name: 9-bicyclo[6.1.0]non-4-ynylmethyl (2,5-dioxopyrrolidin-1-yl) carbonate
• InChIKey: SKTDJYHCSCYLQU-UHFFFAOYSA-N
• INCHI: 1S/C15H17NO5/c17-13-7-8-14(18)16(13)21-15(19)20-9-12-10-5-3-1-2-4-6-11(10)12/h10-12H,3-9H2
• Isomeric SMILES: C1CC2C(C2COC(=O)ON3C(=O)CCC3=O)CCC#C1
• Molecular Weight: 291.3

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolidine-2-ones
• Alternative Parents: Dicarboximides Organic carbonic acids and derivatives Lactams Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: 2-pyrrolidone - Dicarboximide - Carbonic acid derivative - Lactam - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light sensitive，Moisture sensitive，Heat sensitive
• Melt Point(°C): 120 °C