1263166-93-3

Basic information

• Product Name: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane
• Synonyms: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane;(1α,8α,9β)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate;BCN-amine;N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane for Copper-free Click Chemistry;N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl-1,8-diamino-3,6-dioxaoctane;BCN-POE3-NH2
• CAS NO: 1263166-93-3
• Molecular Formula: C₁₇H₂₈N₂O₄
• Molecular Weight: 324.41522
• Mol File: 1263166-93-3.mol

Chemical Properties

• Boiling Point: 487.1±30.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility: Soluble in Water, DMSO, DCM, DMF
• PKA: 12.05±0.46(Predicted)
• CAS DataBase Reference: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane(1263166-93-3)
• EPA Substance Registry System: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane(1263166-93-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1263166-93-3(Hazardous Substances Data)

Usage

Uses

Used in Bioconjugation:
N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane is used as a bioconjugation agent for the formation of stable triazole linkages between azide-tagged biomolecules and other molecules of interest. The reaction occurs without the need for a copper catalyst, simplifying the process and reducing potential side reactions.
Used in Drug Delivery Systems:
In the pharmaceutical industry, N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane is used as a component in the development of drug delivery systems. The amine group can be used to attach drug molecules, while the bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl group can be used to attach targeting moieties, such as azide-tagged antibodies, enabling targeted drug delivery to specific cells or tissues.
Used in Molecular Imaging:
In the field of molecular imaging, N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane is used as a linker to attach imaging agents, such as fluorescent dyes or radiolabels, to biomolecules for tracking their distribution and interaction in living systems.
Used in Material Science:
In material science, N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane can be used as a building block for the development of novel biocompatible materials, taking advantage of its reactive groups for the attachment of various functional molecules.

Upstream product

• 929-59-9 3,6-dioxa-1,8-diaminooctane 
• 1352642-02-4 ((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate 

Downstream Products

• 1393600-24-2 C₂₇H₄₂N₄O₆S 
• 1314639-16-1 C₂₆H₃₇N₃O₉ 

Relevant articles and documents

MODIFIED ANTIBODY, ANTIBODY-CONJUGATE AND PROCESS FOR THE PREPARATION THEREOF

The present invention relates to an antibody comprising a GlcNAc-S(A)x substituent, wherein S(A)x is a sugar derivative comprising x functional groups A wherein A is independently selected from the group consisting of an azido group, a keto group and an alkynyl group and x is 1, 2, 3 or 4, wherein said GlcNAc-S(A)x substituent is bonded to the antibody via CI of the N-acetylglucosamine of said GlcNAc-S(A)x substituent, and wherein said N-acetylglucosamine is optionally fucosylated. The invention also relates to an antibody-conjugate, in particular to an antibody- conjugate according to the Formula (20) or (20b), wherein AB is an antibody, S is a sugar or a sugar derivative, D is a molecule of interest, and wherein said N- acetylglucosamine is optionally fucosylated (b is 0 or 1). The invention further relates to a process for the preparation of a modified antibody, to a process for the preparation of an antibody-conjugate, and to said antibody-conjugate for use as a medicament. In addition, the invention relates to a kit of parts comprising an azide-modified antibody and a linker-conjugate, wherein said linker-conjugate comprises a (hetero)cycloalkynyl group and one or more molecules of interest.

Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are d