Key Documents

744867

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate

Name: (1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate
Brand: ALDRICH

for Copper-free Click Chemistry

Synonym(s):

N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₇NO₅

CAS Number:

1426827-79-3

Molecular Weight:

291.30

MDL number:

MFCD19705416

UNSPSC Code:

12161502

PubChem Substance ID:

329765714

NACRES:

NA.22

Assay:

>90%

Form:

powder

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Quality Level

200

assay

>90%

form

powder

composition

carbon content, 61.85% , hydrogen content, 5.88% , nitrogen content, 4.81%

reaction suitability

reaction type: click chemistry, reagent type: cross-linking reagent

mp

120 °C (248 °F)

solubility

water: insoluble

functional group

NHS ester

storage temp.

−20°C

SMILES string

[H][C@@]12CCC#CCC[C@]1([H])[C@@H]2COC(ON3C(CCC3=O)=O)=O

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/t10-,11+,12-

InChI key

SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Description

Application

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-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.{67
It 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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

View All Articles

?Click? access to multilayer functionalized Au surface: A terpyridine patterning example.

Materials Science and Engineering, C, 75, 1343-1350 (2017)

Recombinant DNA technology and click chemistry: a powerful combination for generating a hybrid elastin-like-statherin hydrogel to control calcium phosphate mineralization.

Misbah MH, et al.

Beilstein Journal of Nanotechnology, 8, 772-772 (2017)

Bio?Orthogonally Crosslinked, Engineered Protein Hydrogels with Tunable Mechanics and Biochemistry for Cell Encapsulation

Madl CM, et al.

Advances in Functional Materials, 26(21), 3612-3620 (2016)

View All Related Papers

Global Trade Item Number

SKU	GTIN
744867-100MG	04061832889344
744867-10MG	04061833425756