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Is there any reaction to bond Amine (-NH2) groups to Hydroxyl...
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+ Hydroxylation
+ Molecular structure
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+ Organic chemistry synthesis
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Luxton the Fox
Is there any reaction to bond Amine (-NH2) groups to Hydroxyl...
Not knowing exactly what you are doing, one other way would be to use a di-isocyanate to couple the amine and the hydroxyl group. You can first react the amine with the isocyanate in any aprotic solvent. Use a molar ratio of NH2/NCO ~ 0.5 to react only one of the NCOs. Use a solvent such as acetone or n-pyrrol at less than 60oC. The reaction of amines with isocyanate is fast and easy. Use the isocyanate-amine adduct for attachment to the polysaccharide. This will have to be conducted in anhydrous conditions which is always a challenge in polysaccharides since residual water may react with NCO. There is plenty of di-isocyanates as free samples from suppliers or from catalogs such as Aldrich.
Not knowing exactly what you are doing, one other way would be to use a di-isocyanate to couple the amine and the hydroxyl group. You can first react the amine with the isocyanate in any aprotic solvent. Use a molar ratio of NH2/NCO ~ 0.5 to react only one of the NCOs. Use a solvent such as acetone or n-pyrrol at less than 60oC. The reaction of amines with isocyanate is fast and easy. Use the isocyanate-amine adduct for attachment to the polysaccharide. This will have to be conducted in anhydrous conditions which is always a challenge in polysaccharides since residual water may react with NCO. There is plenty of di-isocyanates as free samples from suppliers or from catalogs such as Aldrich.
Hydroxyl group and amino group are the both nuclephilic. So no reaction will take place. But when polysaccharide presente on its backbone an anomeric carbone (asymetric carbone) , the situation is completly different. We have here an aldehyde which can easily react with amine to give an imine. See also reducing sugar (equilibrium between the closed form of the cycle and the opened corresponding form). Best regards.
Hydroxyl group and amino group are the both nuclephilic. So no reaction will take place. But when polysaccharide presente on its backbone an anomeric carbone (asymetric carbone) , the situation is completly different. We have here an aldehyde which can easily react with amine to give an imine. See also reducing sugar (equilibrium between the closed form of the cycle and the opened corresponding form). Best regards.
Do you mean that you want to perform a direct reaction with a formation of hydroxylamine derivative R-NH-OR' ? There are some specific reactions; however I think that your real goal is just a conjugation of two molecules. In this case, you have a broad choice of methods based on a functionalization of amine or OH followed by conjugation. For example, you can acylate amine (or OH) with succinic anhydride, e.g. in pyridine or even (for amines) in water. And then react your succinate with nucleophilic component (ROH or RNH2) in the presence of a suitable coupling reagent. It is very simple. If you prepare O-succinate, i.e. RO-COCH2CH2COOH, it can react with amine with amide bond formation in the presence of carbodiimide or other reagent. Or use Mitsunobu or Steglich reaction. There are many variants of this type of coupling.
Do you mean that you want to perform a direct reaction with a formation of hydroxylamine derivative R-NH-OR' ? There are some specific reactions; however I think that your real goal is just a conjugation of two molecules. In this case, you have a broad choice of methods based on a functionalization of amine or OH followed by conjugation. For example, you can acylate amine (or OH) with succinic anhydride, e.g. in pyridine or even (for amines) in water. And then react your succinate with nucleophilic component (ROH or RNH2) in the presence of a suitable coupling reagent. It is very simple. If you prepare O-succinate, i.e. RO-COCH2CH2COOH, it can react with amine with amide bond formation in the presence of carbodiimide or other reagent. Or use Mitsunobu or Steglich reaction. There are many variants of this type of coupling.
You can react the hydroxyl compound with a linking agent( i.e: epichlorohydrin, cyanuric chloride) and treat the product with the amino fictionalized compound.
You can react the hydroxyl compound with a linking agent( i.e: epichlorohydrin, cyanuric chloride) and treat the product with the amino fictionalized compound.
Dear Hossein Shaki -OH group from sugar will react with -NH2 in higher temperature but it's not recommended and no use for your requirement. So that you follow -OH and -NH2 activation and enhance coupling methods by using DIC/DIPEA coupling and activation methods, For this coupling just you give some 30-450C maximum temperature. You prepare O-Succinate means it will react with amine in presence of DIC/DIPEA just like peptide amide bond coupling Hope You Clear.., Good Luck and Regards R.Selva.....
Dear Hossein Shaki -OH group from sugar will react with -NH2 in higher temperature but it's not recommended and no use for your requirement. So that you follow -OH and -NH2 activation and enhance coupling methods by using DIC/DIPEA coupling and activation methods, For this coupling just you give some 30-450C maximum temperature. You prepare O-Succinate means it will react with amine in presence of DIC/DIPEA just like peptide amide bond coupling Hope You Clear.., Good Luck and Regards R.Selva.....
If your synthesis can be modified a bit, and if you were limited to chemical methods only, you could try hydroxylating the amine first (Advanced Synthesis & Catalysis, 2005, 347(9), 1223-1225; J. Org. Chem. 1986, 51(17), 3355-7), and afterwards attaching the sugar component.
If your synthesis can be modified a bit, and if you were limited to chemical methods only, you could try hydroxylating the amine first (Advanced Synthesis & Catalysis, 2005, 347(9), 1223-1225; J. Org. Chem. 1986, 51(17), 3355-7), and afterwards attaching the sugar component.
Hi, yes the pH is important for coupling in aqueous environment, for NH2 typically 8-10. If you can do at least the OH activation with CDI in an organic solvent it would be much better. Otherwise the breakdown of CDI in water is too large for the reaction to work. You can also use mixtures of DMSO-water and similar
Hi, yes the pH is important for coupling in aqueous environment, for NH2 typically 8-10. If you can do at least the OH activation with CDI in an organic solvent it would be much better. Otherwise the breakdown of CDI in water is too large for the reaction to work. You can also use mixtures of DMSO-water and similar
Not knowing exactly what you are doing, one other way would be to use a di-isocyanate to couple the amine and the hydroxyl group. You can first react the amine with the isocyanate in any aprotic solvent. Use a molar ratio of NH2/NCO ~ 0.5 to react only one of the NCOs. Use a solvent such as acetone or n-pyrrol at less than 60oC. The reaction of amines with isocyanate is fast and easy. Use the isocyanate-amine adduct for attachment to the polysaccharide. This will have to be conducted in anhydrous conditions which is always a challenge in polysaccharides since residual water may react with NCO. There is plenty of di-isocyanates as free samples from suppliers or from catalogs such as Aldrich.
Not knowing exactly what you are doing, one other way would be to use a di-isocyanate to couple the amine and the hydroxyl group. You can first react the amine with the isocyanate in any aprotic solvent. Use a molar ratio of NH2/NCO ~ 0.5 to react only one of the NCOs. Use a solvent such as acetone or n-pyrrol at less than 60oC. The reaction of amines with isocyanate is fast and easy. Use the isocyanate-amine adduct for attachment to the polysaccharide. This will have to be conducted in anhydrous conditions which is always a challenge in polysaccharides since residual water may react with NCO. There is plenty of di-isocyanates as free samples from suppliers or from catalogs such as Aldrich.
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Hydroxyl group and amino group are the both nuclephilic. So no reaction will take place. But when polysaccharide presente on its backbone an anomeric carbone (asymetric carbone) , the situation is completly different. We have here an aldehyde which can easily react with amine to give an imine.
See also reducing sugar (equilibrium between the closed form of the cycle and the opened corresponding form). Best regards.
Hydroxyl group and amino group are the both nuclephilic. So no reaction will take place. But when polysaccharide presente on its backbone an anomeric carbone (asymetric carbone) , the situation is completly different. We have here an aldehyde which can easily react with amine to give an imine.
See also reducing sugar (equilibrium between the closed form of the cycle and the opened corresponding form). Best regards.
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Here You have description in our paper, applied in nanoparticles formation:
https://www.researchgate.net/publication/289991753_Dextran_Nanoparticle_Synthesis_and_Properties
Detection of fluorescent organic nanoparticles by confocal laser endomicroscopy in a rat model of Barrett's esophageal adenocarcinoma, International Journal of Nanomedicine 10(default):6811-6823 · October 2015
Article Dextran Nanoparticle Synthesis and Properties
Here You have description in our paper, applied in nanoparticles formation:
https://www.researchgate.net/publication/289991753_Dextran_Nanoparticle_Synthesis_and_Properties
Detection of fluorescent organic nanoparticles by confocal laser endomicroscopy in a rat model of Barrett's esophageal adenocarcinoma, International Journal of Nanomedicine 10(default):6811-6823 · October 2015
Article Dextran Nanoparticle Synthesis and Properties
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Do you mean that you want to perform a direct reaction with a formation of hydroxylamine derivative R-NH-OR' ? There are some specific reactions; however I think that your real goal is just a conjugation of two molecules. In this case, you have a broad choice of methods based on a functionalization of amine or OH followed by conjugation. For example, you can acylate amine (or OH) with succinic anhydride, e.g. in pyridine or even (for amines) in water. And then react your succinate with nucleophilic component (ROH or RNH2) in the presence of a suitable coupling reagent. It is very simple. If you prepare O-succinate, i.e. RO-COCH2CH2COOH, it can react with amine with amide bond formation in the presence of carbodiimide or other reagent. Or use Mitsunobu or Steglich reaction. There are many variants of this type of coupling.
Do you mean that you want to perform a direct reaction with a formation of hydroxylamine derivative R-NH-OR' ? There are some specific reactions; however I think that your real goal is just a conjugation of two molecules. In this case, you have a broad choice of methods based on a functionalization of amine or OH followed by conjugation. For example, you can acylate amine (or OH) with succinic anhydride, e.g. in pyridine or even (for amines) in water. And then react your succinate with nucleophilic component (ROH or RNH2) in the presence of a suitable coupling reagent. It is very simple. If you prepare O-succinate, i.e. RO-COCH2CH2COOH, it can react with amine with amide bond formation in the presence of carbodiimide or other reagent. Or use Mitsunobu or Steglich reaction. There are many variants of this type of coupling.
More
VOTE
You can react the hydroxyl compound with a linking agent( i.e: epichlorohydrin, cyanuric chloride) and treat the product with the amino fictionalized compound.
You can react the hydroxyl compound with a linking agent( i.e: epichlorohydrin, cyanuric chloride) and treat the product with the amino fictionalized compound.
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VOTE
Dear Hossein Shaki
-OH group from sugar will react with -NH2 in higher temperature but it's not recommended and no use for your requirement.
So that you follow -OH and -NH2 activation and enhance coupling methods by using DIC/DIPEA coupling and activation methods,
For this coupling just you give some 30-450C maximum temperature.
You prepare O-Succinate means it will react with amine in presence of DIC/DIPEA just like peptide amide bond coupling
Hope You Clear..,
Good Luck and Regards
R.Selva.....
Dear Hossein Shaki
-OH group from sugar will react with -NH2 in higher temperature but it's not recommended and no use for your requirement.
So that you follow -OH and -NH2 activation and enhance coupling methods by using DIC/DIPEA coupling and activation methods,
For this coupling just you give some 30-450C maximum temperature.
You prepare O-Succinate means it will react with amine in presence of DIC/DIPEA just like peptide amide bond coupling
Hope You Clear..,
Good Luck and Regards
R.Selva.....
More
VOTE
Please, are there mechanism reaction between amin and alcohol at high pH (maillar reaction)
Please, are there mechanism reaction between amin and alcohol at high pH (maillar reaction)
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If your synthesis can be modified a bit, and if you were limited to chemical methods only, you could try hydroxylating the amine first (Advanced Synthesis & Catalysis, 2005, 347(9), 1223-1225; J. Org. Chem. 1986, 51(17), 3355-7), and afterwards attaching the sugar component.
If your synthesis can be modified a bit, and if you were limited to chemical methods only, you could try hydroxylating the amine first (Advanced Synthesis & Catalysis, 2005, 347(9), 1223-1225; J. Org. Chem. 1986, 51(17), 3355-7), and afterwards attaching the sugar component.
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Hi, yes the pH is important for coupling in aqueous environment, for NH2 typically 8-10. If you can do at least the OH activation with CDI in an organic solvent it would be much better. Otherwise the breakdown of CDI in water is too large for the reaction to work. You can also use mixtures of DMSO-water and similar
Hi, yes the pH is important for coupling in aqueous environment, for NH2 typically 8-10. If you can do at least the OH activation with CDI in an organic solvent it would be much better. Otherwise the breakdown of CDI in water is too large for the reaction to work. You can also use mixtures of DMSO-water and similar
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I agree with Nizar. you can also oxidise quantitatively with periodate and then do a reductive amination. Regards. Deon
I agree with Nizar. you can also oxidise quantitatively with periodate and then do a reductive amination. Regards. Deon
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i have partially oxidized OH groups of polymer with periodate and carried out amination. of PEGamine
i have partially oxidized OH groups of polymer with periodate and carried out amination. of PEGamine
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Marius, Read Igor Dubey's answer, above.
Marius, Read Igor Dubey's answer, above.
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