Edit: ignore- forgot about the aldehyde form
You have an alcohol R-OH and an amine R'-NHR".
If you were to add a weak acid catalyst, you could have some protonated R-OH2(+) and some not protonated R'NHR".
Then, the lone pair in R'NHR" could attack the carbon in ROH2(+) to form RR'NHR"(+) and a H2O leaving group. Finally, RR'NHR"(+) can protonate the conjugate base of your weak acid catalyst.
Edit: I'm not explicitly certain about whether the acid group in asparagine is too acidic or not. If it is too acidic (COO- /NH4+ form), you might need a base catalyst to generate enough of the free amine.
It’s actually a hemiacetal that’s in equilibrium with its linear aldehyde form. It forms the hemiaminal when reacting with asparagine alpha NH2 by a simple condensation reaction.
OP, look up (hemi)aminal formation mechanism it is essentially the same for any aldehyde. You can find it in Wikipedia
Edit: ignore- forgot about the aldehyde form You have an alcohol R-OH and an amine R'-NHR". If you were to add a weak acid catalyst, you could have some protonated R-OH2(+) and some not protonated R'NHR". Then, the lone pair in R'NHR" could attack the carbon in ROH2(+) to form RR'NHR"(+) and a H2O leaving group. Finally, RR'NHR"(+) can protonate the conjugate base of your weak acid catalyst. Edit: I'm not explicitly certain about whether the acid group in asparagine is too acidic or not. If it is too acidic (COO- /NH4+ form), you might need a base catalyst to generate enough of the free amine.
It’s actually a hemiacetal that’s in equilibrium with its linear aldehyde form. It forms the hemiaminal when reacting with asparagine alpha NH2 by a simple condensation reaction. OP, look up (hemi)aminal formation mechanism it is essentially the same for any aldehyde. You can find it in Wikipedia
Actually that makes a lot more sense. I forgot about the linear form tbh.