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83173

Sigma-Aldrich

D-Pyroglutamic acid ethyl ester

puriss., ≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

(R)-5-Oxoproline ethyl ester, D-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C7H11NO3
CAS Number:
68766-96-1
Molecular Weight:
157.17
Beilstein/REAXYS Number:
82622
MDL number:
MFCD00010848
UNSPSC Code:
12352200
PubChem Substance ID:
329769279

grade

puriss.

assay

≥99.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D −4.0±1.0°, c = 10% in ethanol

optical purity

enantiomeric ratio: ≥99:1 (GC)

mp

53-57 °C

application(s)

peptide synthesis

SMILES string

CCOC(=O)[C@H]1CCC(=O)N1

InChI

1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1

InChI key

QYJOOVQLTTVTJY-RXMQYKEDSA-N

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Other Notes

This ester of pyroglutamic acid can be transformed in many ways, e.g. N-alkylation[1]; Thionation of the lactam[2]; Preparation of the aldehyde[3]; Reduction to the hydroxymethyl compound[4]

replaced by

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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T C Friedman et al.
Biochemistry, 24(15), 3907-3913 (1985-07-16)
Pyroglutamyl-peptide hydrolase (EC 3.4.11.8) removes the N-terminal pyroglutamyl residue from pyroglutamyl-containing peptides such as thyrotropin-releasing hormone (TRH), luteinizing hormone-releasing hormone (LH-RH), neurotensin, and bombesin. The aldehyde analogue of pyroglutamate, 5-oxoprolinal, was synthesized as an active site directed transition-state inhibitor of
U. Burkard et al.
Liebigs Ann. Chem., 1030-1030 (1986)
T.P. Andersen et al.
Liebigs Ann. Chem., 269-269 (1986)
R.B. Silverman et al.
The Journal of Organic Chemistry, 45, 815-815 (1980)

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