In
organic chemistry, a Schiff base (named after
Hugo Schiff) is a compound with the general structure R1R2C=NR3 (R3 =
alkyl or
aryl, but not
hydrogen).[1][2] They can be considered a sub-class of
imines, being either secondary
ketimines or secondary
aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from
anilines.[3] The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. R−CH=NR' where R' ≠ H).[4]
Schiff bases have been investigated in relation to a wide range of contexts, including antimicrobial, antiviral and anticancer activity. They have also been considered for the inhibition of
amyloid-β aggregation.[6]
Schiff bases are common enzymatic intermediates where an amine, such as the terminal group of a lysine residue, reversibly reacts with an aldehyde or ketone of a cofactor or substrate. The common enzyme cofactor
pyridoxal phosphate (PLP) forms a Schiff base with a lysine residue and is transaldiminated to the substrate(s).[7] Similarly, the cofactor
retinal forms a Schiff base in
rhodopsins, including human rhodopsin (via Lysine 296), which is key in the photoreception mechanism.
Conjugated Schiff bases absorb strongly in the UV-visible region of the electromagnetic spectrum. This absorption is the basis of the
anisidine value, which is a measure of oxidative spoilage for fats and oils.
Schiff, Ugo (1866).
"Sopra una nova serie di basi organiche" [On a new series of organic bases]. Giornale di Scienze Naturali ed Economiche (in Italian). 2: 201–257.
Schiff, Hugo (1866).
"Eine neue Reihe organischer Diamine" [A new series of organic diamines]. Annalen der Chemie und Pharmacie, Supplementband (in German). 3: 343–370.
^Bajema, Elizabeth A.; Roberts, Kaleigh F.; Meade, Thomas J. (2019). "Chapter 11. Cobalt-Schiff Base Complexes:Preclinical Research and Potential Therapeutic Uses". In Sigel, Astrid; Freisinger, Eva; Sigel, Roland K. O.; Carver, Peggy L. (eds.). Essential Metals in Medicine:Therapeutic Use and Toxicity of Metal Ions in the Clinic. Metal Ions in Life Sciences. Vol. 19. Berlin: de Gruyter GmbH. pp. 267–301.
doi:
10.1515/9783110527872-017.
ISBN978-3-11-052691-2.
PMID30855112.
S2CID73727460.
In
organic chemistry, a Schiff base (named after
Hugo Schiff) is a compound with the general structure R1R2C=NR3 (R3 =
alkyl or
aryl, but not
hydrogen).[1][2] They can be considered a sub-class of
imines, being either secondary
ketimines or secondary
aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from
anilines.[3] The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. R−CH=NR' where R' ≠ H).[4]
Schiff bases have been investigated in relation to a wide range of contexts, including antimicrobial, antiviral and anticancer activity. They have also been considered for the inhibition of
amyloid-β aggregation.[6]
Schiff bases are common enzymatic intermediates where an amine, such as the terminal group of a lysine residue, reversibly reacts with an aldehyde or ketone of a cofactor or substrate. The common enzyme cofactor
pyridoxal phosphate (PLP) forms a Schiff base with a lysine residue and is transaldiminated to the substrate(s).[7] Similarly, the cofactor
retinal forms a Schiff base in
rhodopsins, including human rhodopsin (via Lysine 296), which is key in the photoreception mechanism.
Conjugated Schiff bases absorb strongly in the UV-visible region of the electromagnetic spectrum. This absorption is the basis of the
anisidine value, which is a measure of oxidative spoilage for fats and oils.
Schiff, Ugo (1866).
"Sopra una nova serie di basi organiche" [On a new series of organic bases]. Giornale di Scienze Naturali ed Economiche (in Italian). 2: 201–257.
Schiff, Hugo (1866).
"Eine neue Reihe organischer Diamine" [A new series of organic diamines]. Annalen der Chemie und Pharmacie, Supplementband (in German). 3: 343–370.
^Bajema, Elizabeth A.; Roberts, Kaleigh F.; Meade, Thomas J. (2019). "Chapter 11. Cobalt-Schiff Base Complexes:Preclinical Research and Potential Therapeutic Uses". In Sigel, Astrid; Freisinger, Eva; Sigel, Roland K. O.; Carver, Peggy L. (eds.). Essential Metals in Medicine:Therapeutic Use and Toxicity of Metal Ions in the Clinic. Metal Ions in Life Sciences. Vol. 19. Berlin: de Gruyter GmbH. pp. 267–301.
doi:
10.1515/9783110527872-017.
ISBN978-3-11-052691-2.
PMID30855112.
S2CID73727460.