Method for cleaving amide bonds
A method for cleaving amide bonds, comprising: a) providing a molecule comprising an amide group; b) reacting the molecule comprising an amide group with hydroxylamine (NH 2 OH) or a salt thereof to cleave the amide bond of the amide group.
1. A method for cleaving amide bonds in glycosaminoglycans, the method comprising reacting a glycosaminoglycan (GAG) comprising an N-acyl amide group with hydroxylamine (NH 2 OH) or a salt thereof to cleave the amide bond of the amide group.
2. The method according to claim 1 , further comprising recovering a product formed by the reaction.
3. The method according to claim 1 , wherein the GAG comprises a pH sensitive chiral center.
4. The method according to claim 1 , wherein the GAG comprises a pH sensitive protecting group.
5. The method according to claim 1 , wherein the reacting is at a temperature of 100° C. or less.
6. The method according to claim 1 , wherein the reacting is for 2-200 hours.
7. The method according to claim 1 , wherein the reacting is in water.
8. The method according to claim 1 , wherein having a molar concentration of hydroxylamine in the range of 5-20 M.
9. The method according to claim 1 , wherein the GAG is reacted with a hydroxylamine salt.
10. The method according to claim 9 , wherein the hydroxylamine salt is a salt of hydroxylamine and hydroiodic acid or trifluoroacetic acid.
11. The method according to claim 9 , having a concentration of the hydroxylamine salt in the range of 0.1-5 M.
12. The method according to claim 9 , wherein the reaction is performed in a solvent capable of at least partially dissolving the hydroxylamine salt.
13. The method according to claim 1 , wherein the reaction is performed at a pH value in the range of 4-12.
14. The method according to claim 13 , wherein the reaction is performed at a pH value in the range of 9-11.
15. The method according to claim 13 , further comprising lowering the pH of the reaction to a value in the range of 4-9 by adding a pH reducing agent selected from the group consisting of mineral acids, organic acids and pH reducing salts, and combinations thereof.
16. The method according to claim 15 , wherein the pH reducing agent is a pH reducing salt.
17. The method according to claim 1 , wherein the GAG is selected from hyaluronic acid, hyaluronan, chondroitin, chondroitin sulphate, heparin sulphate, heparosan, heparin, dermatan sulphate, keratin sulphate, and combinations thereof.
18. The method according to claim 17 , wherein the GAG is hyaluronic acid.
19. The method according to claim 1 , wherein the GAG is crosslinked in a hydrogel.
20. The method according to claim 1 , having a concentration of the hydroxylamine salt in the range of 0.1-10 M.
21. The method according to claim 1 , further comprising recovering a product of the reacted GAGs exhibiting a weight average molecular weight of at least about 1,000 kDa.