LIPID MAPS

Structure Database (LMSD)

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Common Name

PCTR2

Systematic Name

16R-(S-cysteinylglycinyl)-17S-hydroxy-4Z,7Z,10Z,12E,14E,19Z-docosahexaenoic acid

Synonyms

Protectin Conjugates in Tissue Regeneration 2

LM ID

LMFA04040005

Formula

C₂₇H₄₀N₂O₆S

Exact Mass

Calculate m/z

520.26071

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Protein conjugates in tissue regeneration 2 (PCTR2) is a specialized pro-resolving mediator (SPM) synthesized from docosahexaenoic acid (DHA).^1,2 DHA is oxidized to 16S,17S-epoxy-protectin, which is converted to PCTR1 by glutathione S-transferase and to PCTR2 via γ-glutamyl transpeptidase.¹ PCTR2 is found in resolving mouse exudate and in both M1 and M2 macrophages differentiated from isolated human monocytes.^3,4

This information has been provided by Cayman Chemical

References

1. Aursnes, M., Tungen, J.E., Colas, R.A., et al. Synthesis of the 16S,17S-epoxyprotectin intermediate in the biosynthesis of protectins by human macrophages. J. Nat. Prod. 8(12), 2924-2931 (2015).

2. Ramon, S., Dalli, J., Sanger, J.M., et al. The protectin PCTR1 is produced by human M2 macrophages and enhances resolution of infectious inflammation. Am. J. Pathol. 186(4), 962-973 (2016).

3. Rodriguez, A.R., and Spur, B.W. Total synthesis of pro-resolving and tissue-regenerative protectin sulfido-conjugates. Tetrahedron Lett. 56(42), 5811-5815 (2015).

4. Serhan, C.N., Dalli, J.P., and Chiang, N. Oxylipin-peptide conjugated mediators that promote resolution of infection, organ protection and tissue regeneration. US20170258806 A1, (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates,
Tetrahedron Letts, 2015

DOI: 10.1016/j.tetlet.2015.09.020

String Representations

InChiKey (Click to copy)

WUKLNYKELYBPSU-WRSKGJTLSA-N

InChi (Click to copy)

InChI=1S/C27H40N2O6S/c1-2-3-14-17-23(30)24(36-21-22(28)27(35)29-20-26(33)34)18-15-12-10-8-6-4-5-7-9-11-13-16-19-25(31)32/h3,5-8,10-15,18,22-24,30H,2,4,9,16-17,19-21,28H2,1H3,(H,29,35)(H,31,32)(H,33,34)/b7-5-,8-6-,12-10+,13-11-,14-3-,18-15+/t22-,23-,24+/m0/s1

SMILES (Click to copy)

C(CC/C=C\C/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)NCC(O)=O)N)[C@@H](O)C/C=C\CC)(=O)O