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.