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Key Documents

C4187

Sigma-Aldrich

Cyanoborohydride Coupling Buffer

Synonym(s):

Coupling buffer

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About This Item

UNSPSC Code:
12161700
NACRES:
NA.56

form

liquid

reaction suitability

reagent type: reductant

technique(s)

affinity chromatography: suitable

application(s)

life science and biopharma

storage temp.

2-8°C

Application

A ready-to-use reagent used to couple amine ligands to aldehyde functional groups. The coupling buffer reaction is a reductive amination of the intermediate Schiff′s base to a stable C−N bond.
Cyanoborohydride Coupling Buffer has been used:
  • in coupling reactions between amines and glutaraldehyde
  • to reduce hydrazone bond to a stable hydrazide bond
  • as a component in oligonucleotide reaction mixture for coverslips functionalization

Cyanoborohydride Coupling Buffer is used in affinity chromatography, protein chromatography, activated/functionalized matrices and synthetic reagents. Cyanoborohydride has been used to inform a safe and effective gene-transfer system targeting hepatocytes as well as to develop a method for targeted delivery of anticancer therapeutics to cancer cells in hypoxic areas.

Biochem/physiol Actions

Cyanoborohydride Coupling Buffer is a reagent suitable for reductive amination processes, that contributes to transformation of simple alcohols into more complex amines. It is used in the conversion of Schiff base, by reducing it, to form a secondary amine without affecting aldehyde groups on the support.

Components

0.02 M sodium phosphate, pH 7.5, containing 0.2 M sodium chloride and 3.0 g/L sodium cyanoborohydride

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Use of polymer supported reagents for clean multi-step organic synthesis: preparation of amines and amine derivatives from alcohols for use in compound library generation
Ley S, et al.
Journal of the Chemical Society. Perkin Transactions 1, 15(27), 2239-2242 (1998)
Christopher A Holden et al.
International journal of nanomedicine, 5, 25-36 (2010-02-18)
Tumors frequently contain hypoxic regions that result from a shortage of oxygen due to poorly organized tumor vasculature. Cancer cells in these areas are resistant to radiation- and chemotherapy, limiting the treatment efficacy. Macrophages have inherent hypoxia-targeting ability and hold
Direct electrical detection of antigen?antibody binding on diamond and silicon substrates using electrical impedance spectroscopy.
Yang W, et al.
Analyst, 132(4), 296-306 (2007)
Binding between the integrin ?X?2 (CD11c/CD18) and heparin.
Vorup-Jensen T, et al.
Test, 282(42), 30869-30877 (2007)
Polymer-supported triacetoxyborohydride: a novel reagent of choice for reductive amination
Bhattacharyya S, et al.
Tetrahedron Letters, 44(27), 4957-4960 (2003)

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