Pyrohomoglutamic acid, D-

Pyrohomoglutamic acid, D-

$65.00 - 1 mg

$230.00 - 5 mg

All prices in Australian dollars

Code
BIA-P2221
Synonyms
(2R)-6-Oxo-2-piperidinecarboxylic acid
CAS #
72002-30-3
Molecular Formula
C6H9NO3
Molecular Weight
143.14
Purity
>95% by HPLC
Long Term Storage
-20°C
Solubility
Soluble in methanol or DMSO

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Application Notes

D-Pyrohomoglutamic acid (R-6-oxopiperidine-2-carboxylic acid) is a δ-lactam formed by the head-to-tail cyclisation of D-homoglutamic acid. Unlike pyroglutamic acid, D-pyrohomoglutamic acid is reported as a pyrolysis product but is re-named to better reflect the compound’s structural relationship to D-homoglutamic acid, the “unnatural” optical isomer of L-homoglutamic acid. D-Pyrohomoglutamic acid has found limited application as a terminal amino acid analogue in the structure-activity relationships of small linear peptides such as substance P and as a chemical synthon. The biological and pharmacological properties of D-pyrohomoglutamic acid have not been extensively investigated.

References

  • Syntheses and biological activities of substance P analogs containing L- and D-homoglutamine and L- and D-pyrohomoglutamic acid at position 5 and 6. Hashimoto T. et al. Bull Chem Soc Jpn. 1987, 60, 1207.
  • Discovery of highly selective inhibitors of the immunoproteasome low molecular mass polypeptide 2 (LMP2) subunit. Johnson H.W.B. et al. ACS Med Chem Lett. 2017, 8, 413.

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