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Merck
모든 사진(1)

문서

744867

Sigma-Aldrich

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

for Copper-free Click Chemistry

동의어(들):

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

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모든 사진(1)

About This Item

실험식(Hill 표기법):
C15H17NO5
CAS Number:
1426827-79-3
Molecular Weight:
291.30
UNSPSC 코드:
12161502
PubChem Substance ID:
329765714
NACRES:
NA.22

형태

powder

구성

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

반응 적합성

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

작용기

NHS ester

저장 온도

−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

애플리케이션

(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.

포장

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

시험 성적서(COA)

제품의 로트/배치 번호를 입력하여 시험 성적서(COA)을 검색하십시오. 로트 및 배치 번호는 제품 라벨에 있는 ‘로트’ 또는 ‘배치’라는 용어 뒤에서 찾을 수 있습니다.

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문서

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.

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