L-Pyroglutamic Acid → 5-Oxo-L-prolyl-L-glutamine

HRID 1760151Notes

Reaction equation

[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.C(Cl)(=O)C(C)(C)C.C([O:21][C:22](=[O:30])[C@H:23]([CH2:25][CH2:26][C:27](=[O:29])[NH2:28])[NH2:24])(C)(C)C>>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:24][C@H:23]([C:22]([OH:30])=[O:21])[CH2:25][CH2:26][C:27](=[O:29])[NH2:28])=[O:9]

Participants

Reactant 3

HCID 7405L-Pyroglutamic Acid

HCID 62493Pivaloyl chloride

HCID 5287779HCID 5287779, compound

Product 1

HCID 110106215-Oxo-L-prolyl-L-glutamine

Procedure

A mixed anhydride from L-pyroglutamic acid 9 and pivaloyl chloride was coupled with L-glutamine t-butyl ester 10 followed by acidic workup to yield L-pyroglutamyl-L-glutamine 7 (Equation 2). This dipeptide was purified by reversed phase HPLC using a gradient system of acetonitrile/H2O.

Sources & evidence

ORD record: ord-59ef154b662045288986d2e4bfa7b4f4
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841530B2

Reaction notes

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