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RESID:AA0037
O-phospho-L-serine

Alternate names:
2-amino-3-hydroxypropanoic acid 3-phosphate;
2-azanyl-3-(phosphonooxy)propanoic acid;
O-phosphonoserine;
O3-phosphoserine;
serine phosphate ester

Systematic name:
(2S)-2-amino-3-(phosphonooxy)propanoic acid
Cross-references: CAS:407-41-0; ChEBI:45522; PDBHET:SEP

Dates:
Created: 31-Mar-1995
Structure revised: 31-Mar-1995
Text changed: 31-Dec-2011

Formula: C 3 H 6 N 1 O 5 P 1
Formula weight: #chem 167.06 #phys 166.998359

Correction formula: C 0 H 1 N 0 O 3 P 1
Correction weight: #chem 79.98 #phys 79.966331
Based on AA0016

Reference 1:
Authors: Lipmann, F.A.; Levene, P.A.
Journal: J. Biol. Chem. 98, 109-114, 1932
Title: Serinephosphoric acid obtained on hydrolysis of vitellinic acid.
Note: phosphoserine isolated from a protein hydrolysate

Reference 2:
Authors: Fischer, E.H.; Graves, D.J.; Crittenden, E.R.; Krebs, E.G.
Journal: J. Biol. Chem. 234, 1698-1704, 1959
Title: Structure of the site phosphorylated in the phosphorylase b to a reaction.
Cross-references: PMID:13672948
Note: radiolabeling, determination of peptide sequence, demonstration of specific enzymatic production and removal

Reference 3:
Authors: Clark, R.C.
Journal: Int. J. Biochem. 17, 983-988, 1985
Title: The primary structure of avian phosvitins. Contributions through the Edman degradation of methylmercaptovitins prepared from the constituent phosphoproteins.
Cross-references: DOI:10.1016/0020-711X(85)90243-5; PMID:4065410
Note: phosphoserine converted to dl-S-methylcysteine for phenylthiohydantoin identification

Reference 4:
Authors: Price, P.A.; Rice, J.S.; Williamson, M.K.
Journal: Protein Sci. 3, 822-830, 1994
Title: Conserved phosphorylation of serines in the Ser-X-Glu/Ser(P) sequences of the vitamin K-dependent matrix Gla protein from shark, lamb, rat, cow, and human.
Cross-references: DOI:10.1002/pro.5560030511; PMID:8061611
Note: improved methodology for conversion to dl-S-methylcysteine

Reference 5:
Authors: Knight, Z.A.; Schilling, B.; Row, R.H.; Kenski, D.M.; Gibson, B.W.; Shokat, K.M.
Journal: Nature Biotechnol. 21, 1047-1054, 2003
Title: Phosphospecific proteolysis for mapping sites of protein phosphorylation.
Cross-references: DOI:10.1038/nbt863; PMID:12923550
Note: method for converting phosphoserine and phosphothreonine to analogs of lysine for enzymatic analysis

Reference 6:
Authors: Park, H.S.; Hohn, M.J.; Umehara, T.; Guo, L.T.; Osborne, E.M.; Benner, J.; Noren, C.J.; Rinehart, J.; Söll, D.
Journal: Science 333, 1151-1154, 2011
Title: Expanding the genetic code of Escherichia coli with phosphoserine.
Cross-references: DOI:10.1126/science.1207203; PMID:21868676
Note: engineered system for encoding phosphoserine as a pretranslational modification

Generating Enzyme:
protein-serine kinase (EC 2.7.1.37)

Sequence code: S
Cross-references: GO:0018105; GO:0018331; PSI-MOD:00046

Source: natural

Keywords: phosphoprotein

UniProt Features
ACT_SITE Phosphoserine intermediate
MOD_RES Phosphoserine


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Copyright © 2001, 2014 John S. Garavelli

CONTACT:
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