Isoserine

Isoserine
Names
IUPAC name
3-Amino-2-hydroxypropanoic acid
Other names
3-Aminolactic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C3H7NO3/c4-1-2(5)3(6)7/h2,5H,1,4H2,(H,6,7)
    Key: BMYNFMYTOJXKLE-UHFFFAOYSA-N
  • C(C(C(=O)O)O)N
Properties
C3H7NO3
Molar mass 105.093 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isoserine is a non-proteinogenic α-hydroxy-β-amino acid, and an isomer of serine. Non-proteinogenic amino are not part of the genetic code of any known organism and are only present in proteins if added post-translationally. Isoserine has only been produced synthetically.

The first documented synthesis of isoserine in a laboratory setting was by Miyazawa et al., who published their results in 1976.[1]

See also

References

  1. ^ Ziora, Zyta; Skwarcynski, Mariusz; Kiso, Yoshiaki (2011). "Medicinal Chemistry of α-Hydroxy-β-Amino Acids". In Hughes, Andrew B. (ed.). Amino Acids, Peptides and Proteins in Organic Chemistry, Volume 4: Protection, Reactions, Medicinal Chemistry, Combinatorial Synthesis. Wiley-VCH. Section 6.2.2: Synthesis of α-Hydroxy-β-amino acids. ISBN 978-3-527-63182-7. OCLC 741558720. Retrieved 2017-06-10 – via Google Books.


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