Low-barrier hydrogen bond between phosphate and the amide group in phosphopeptide.
As the conversion between the monoionic (1) and diionic (2) form of the phosphate occurs, the phosphorylated peptides or proteins can not only cause the formation of a hydrogen bond between the phosphate group and the amide group but also change the strength of the hydrogen bond to form low-barrier hydrogen bonds (LBHBs). This reversible protonation of the phosphate group, which changes both the electrostatic properties of the phosphate group and the strength of the hydrogen bond, provides a possible mechanism in regulating protein function.
Du
Jin-Tang
JT
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Li
Yan-Mei
YM
Wei
Wei
W
Wu
Guo-Shi
GS
Zhao
Yu-Fen
YF
Kanazawa
Kenji
K
Nemoto
Tadashi
T
Nakanishi
Hiroshi
H
D000577:Amides / Q000737:chemistry*; D006801:Humans; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D010748:Phosphopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D016875:tau Proteins / Q000737:chemistry
D000577:Amides; D010710:Phosphates; D010748:Phosphopeptides; D016875:tau Proteins