I want to conjugate FITC dye to a molecule having secondary amine (>NH). The -N=C=S group of FITC should be used keeping the -COOH group intact. I do not wish to change the target molecule as it will alter its properties. I have come across various literature where FITC is conjugated to other molecule having primary amine (-NH2) group. So, can FITC be conjugated to a molecule having primary amine? Any help in terms of ideas or literature will be of great help. Thank you in advance.
Dear Ranjit, please read this article
"Propargylamine–isothiocyanate reaction: efficient conjugation chemistry in aqueous media"
H. M.-F. Viart,a T. S. Larsen,a C. Tassone,b T. L. Andresenbc and M. H. Clausen
I suppose you should avoid heating
My best regards,
Antonina
I think you can. ButI would like somebody to confirm it either than myself
FITC can be conjugated to primary amine containing molecules for sure. however, i am bit doubtful how efficient it will be with secondary amines (steric considerations). reference above by Antonina does indicate the reaction going forward with secondary amine. but, i think this is because of the presence of alkyne which may be playing a significant role here. so a pure secondary amine, i am doubtful.
Dear Ranjit De many thanks for your interesting technical question. I'm pretty sure that this reaction will, be possible. In this context please have a look at the following relevant article:
Reaction of fluorescein-isothiocyanate with proteins and amino acids. I. Covalent and non-covalent binding of fluorescein-isothiocyanate and fluorescein to proteins
Article Reaction of Fluorescein-Isothiocyanate with Proteins and Ami...
This article is freely available as public full text on RG and can be downloaded as pdf file.
Hello! Can anyone let me know the mechanism of FITC reaction with amine?
Dear Ayesha Seth thank you for your kind response and question. The cyclization reaction between propargylamines and isothiocyanates has already been discovered in the year 1964 and published in the ACS Journal of Organic Chemistry:
Reactions of Acetylenic Amines. VIII. Cyclization of Acetylenic Ureas
https://pubs.acs.org/doi/abs/10.1021/jo01030a044?journalCode=joceah&quickLinkVolume=29&quickLinkPage=1851&selectedTab=citation&volume=29
Unfortunately this article has not been posted as public full text on RG. Perhaps you can access it through your institution. The reaction is also discussed in the following relevant reference:
Propargylamine-isothiocyanate reaction: efficient conjugation chemistry in aqueous media
Article ChemInform Abstract: Propargylamine-Isothiocyanate Reaction:...
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