Trimethylsilyl pipecolate

Trimethylsilyl pipecolate
Names
IUPAC name
Trimethylsilyl piperidine-2-carboxylate
Other names
  • 2-piperidinecarboxylic acid, trimethylsilyl ester
  • Pipecolic acid TMS derivative
  • Pipecolic acid-monoTMS
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C9H19NO2Si/c1-13(2,3)12-9(11)8-6-4-5-7-10-8/h8,10H,4-7H2,1-3H3
    Key: FPPDHYMXBHTGOC-UHFFFAOYSA-N
  • C[Si](C)(C)OC(=O)C1CCCCN1
Properties
C6H10NO2Si(CH3)3
Molar mass 201.341 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylsilyl pipecolate is a chemical compound. It is the trimethylsilyl ester of the non-proteinogenic amino acid pipecolic acid.

It is used in gas chromatography–mass spectrometry as the product of derivatisation of pipecolic acid with trimethylsilylating agents such as MSTFA.[1][2] GC-MS analysis of trimethylsilyl pipecolates can be used to analyse presence of pipecolic acids and their hydroxy derivatives.[3]

It also occurs as a reaction intermediate in organic synthesis, where the trimethylsilyl ester acts as a protecting group for the carboxylic acid moiety in reactions targeting the amine.[4][5]

Preparation

Treatment of pipecolic acid with MSTFA produces trimethylsilyl pipecolate and the N-trimethylsilyl derivative.[6]

Sources

  1. ↑ Holmes, Eric C.; Chen, Yun-Chu; Sattely, Elizabeth S.; Mudgett, Mary Beth (2019). "An engineered pathway for N -hydroxy-pipecolic acid synthesis enhances systemic acquired resistance in tomato". Science Signaling. 12 (604) eaay3066. doi:10.1126/scisignal.aay3066. PMC 7954083. PMID 31641079.
  2. ↑ Hartmann, Michael; Kim, Denis; Bernsdorff, Friederike; Ajami-Rashidi, Ziba; Scholten, Nicola; Schreiber, Stefan; Zeier, Tatyana; Schuck, Stefan; Reichel-Deland, Vanessa; Zeier, Jürgen (2017). "Biochemical Principles and Functional Aspects of Pipecolic Acid Biosynthesis in Plant Immunity". Plant Physiology. 174 (1): 124–153. doi:10.1104/pp.17.00222. PMC 5411157. PMID 28330936.
  3. ↑ Kite, Geoffrey C.; Hughes, Michael J. (1997). "Analysis of hydroxypipecolic acids by gas chromatography-mass spectrometry". Phytochemical Analysis. 8 (6): 294–301. doi:10.1002/(SICI)1099-1565(199711/12)8:6<294::AID-PCA372>3.0.CO;2-R.
  4. ↑ Yoon, Hye-Ran; An, Yong-Wun (2010). "Determination of pipecolic acid following trimethylsilyl and trifluoroacyl derivatisation on plasma filter paper by stable isotope GC-MS for peroxisomal disorders". Archives of Pharmacal Research. 33 (2): 317–323. doi:10.1007/s12272-010-0218-1. PMID 20195834.
  5. ↑ Daniel Lednicer (2008). Organic Chemistry of Drug Synthesis. Vol. 7. Hoboken, NJ: John Wiley & Sons. p. 119. ISBN 978-0-470-10750-8.
  6. ↑ Rodríguez-Sánchez, S.; Hernández-Hernández, O.; Ruiz-Matute, A.I.; Sanz, M.L. (2011). "A derivatization procedure for the simultaneous analysis of iminosugars and other low molecular weight carbohydrates by GC–MS in mulberry (Morus sp.)". Food Chemistry. 126: 353–359. doi:10.1016/j.foodchem.2010.10.097.
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