Displacement reactions of acyclic carbohydrate derivatives. Part III. Aldehyde group participation in 2,3,5-tri-O-benzyl-4-O-toluene-p-sulphonyl-aldehydo-D-ribose

1967 ◽  
pp. 1186
Author(s):  
N. A. Hughes ◽  
P. R. H. Speakman
Keyword(s):  
Aldehyde Group ◽  
Group Participation ◽  
Displacement Reactions

Neighbouring group participation of thiol through aldehyde group assisted thiolysis of active ether: ratiometric and vapor phase fast detection of hydrogen sulfide in mixed aqueous media

2015 ◽  
Vol 39 (7) ◽  
pp. 5669-5675 ◽  
Author(s):  
Avijit Kumar Das ◽  
Shyamaprosad Goswami ◽  
Ching Kheng Quah ◽  
Hoong-Kun Fun
Keyword(s):  
Hydrogen Sulfide ◽  
Vapor Phase ◽  
Aqueous Media ◽  
Aldehyde Group ◽  
Nucleophilic Attack ◽  
Ether Linkage ◽  
Fast Detection ◽  
Group Participation ◽  
Neighbouring Group Participation

Ratiometric and fast detection of H2S via NGP of thiol rather than direct nucleophilic attack to cleave active ether linkage.

Aldehyde gold clusters for molecular labeling

1995 ◽  
Vol 53 ◽  
pp. 858-859
Author(s):  
James F. Hainfeld ◽  
Frederic R. Furuya
Keyword(s):  
Covalent Bond ◽  
Aldehyde Group ◽  
Gold Clusters ◽  
Side Reactions ◽  
Amino Groups ◽  
Sodium Cyanoborohydride ◽  
Schiff’S Base ◽  
Protein Molecules ◽  
Hydroxysuccinimide Esters ◽  
Primary Amino

Glutaraldehyde is a useful tissue and molecular fixing reagents. The aldehyde moiety reacts mainly with primary amino groups to form a Schiff's base, which is reversible but reasonably stable at pH 7; a stable covalent bond may be formed by reduction with, e.g., sodium cyanoborohydride (Fig. 1). The bifunctional glutaraldehyde, (CHO-(CH2)3-CHO), successfully stabilizes protein molecules due to generally plentiful amines on their surface; bovine serum albumin has 60; 59 lysines + 1 α-amino. With some enzymes, catalytic activity after fixing is preserved; with respect to antigens, glutaraldehyde treatment can compromise their recognition by antibodies in some cases. Complicating the chemistry somewhat are the reported side reactions, where glutaraldehyde reacts with other amino acid side chains, cysteine, histidine, and tyrosine. It has also been reported that glutaraldehyde can polymerize in aqueous solution. Newer crosslinkers have been found that are more specific for the amino group, such as the N-hydroxysuccinimide esters, and are commonly preferred for forming conjugates. However, most of these linkers hydrolyze in solution, so that the activity is lost over several hours, whereas the aldehyde group is stable in solution, and may have an advantage of overall efficiency.

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