Sodium pyroglutamate

Two active substances (A-1 and A-2) from A. hlazei with the aid of a Matrigei-induced angiogenesis assay system Table (11) and Fig. (14) . A-1 was identified as sodium pyroglutamate based on the... 

Synonyms 5-Oxo-DL-proline, sodium salt 5-Oxo-L-proline, sodium salt PCA-Na PCA Soda Sodium 5-oxo-L-prolinate Sodium pyroglutamate Sodium DL-2-pyrrolidone-5-carboxylate Sodium L-2-pyrrolidone-5-carboxylate... 

Sodium pyroglutamate. See Sodium PCA Sodium pyrophosphate n-Sodium pyrophosphate. See Tetrasodium pyrophosphate... 

The same intermediate 74 was synthesized by J. W. Bruin et al74 by an alternative route. They reduced the ester function of the pyroglutamate with LiBH4 to the primary alcohol 75a which was protected as the acetate 75b to prevent O-alkylation. Reaction of the sodium salt of 75 b formed with NaH in dimethylformamide, with methyl-7-bromoheptanoate followed by methanolysis of the acetate function gave 74. Oxydation of the alcohol 74 by Pfitzner-Moffat-oxydation or oxydation with Collins reagent led to the unstable aldehyde 77. 

Lhommet and co-workers synthesized (- )-436 by the route shown in Scheme 66 [422). Wittig-Homer reaction between the 2,5-rrans -disubstituted pyrrolidine aldehyde 509, made from (S)-pyroglutamic acid [423), and the protected keto-phosphonate 510 introduced all the skeletal carbon atoms of the target. Simultaneous hydrogenation and //-deprotection of enone 511 gave the aminoketone 512, which spontaneously formed the bicyclic enamine 513 in 98% yield when exposed to trifluoroacetic acid—apparently the first time that such an intermediate has actually been isolated en route to indolizidines. Reduction with sodium cyanoborohydride in acidic medium acid produced a diastereomeric mixture (92 8) of (- )-436 and (+ )-437. The former was isolated in 84% yield after chromatography on silica gel. The overall yield of this 15-step sequence was 8% based on (S)-pyroglutamic acid. 

Figure 4.106 Separation of blocked and W-1-peptides after treatment with pyroglutamate aminopeptidase. Separator column ProPac WCX-10 eluent (A) 0.02 mol/L sodium phosphate (pH 4.8) and (B) 0.02 mol/L sodium phosphate +1 mol/L NaCI (pH 4.8) gradient linear, 0% b to 60% B in 15 min flow rate ...

Fig. 3-219. Separation of blocked and N-l-peptides after treatment with pyroglutamate aminopeptidase. - Separator column ProPac WCX-10 eluant (A) 0.02 mol/L sodium phosphate, pH 4.8, (B) 0.02 mol/L sodium phosphate, pH 4.8 + 1 mol/L Nad gradient linear, 0% B to 60% B in 15 min flow rate 1 mL/min detection UV (220 nm) samples A. pGlu-Ser-Leu-Arg-Trp-amide 4- pyroglutamate aminopeptidase, B. pGlu-Ser-Leu-Arg-Trp-amide, C. neurotensin -i- pyroglutamate aminopeptidase, D. neurotensin (pGlu-Leu-Tyr-Gln-Asn-Lys-Pro-Arg-Arg-Pro-Tyr-lle-Leu), E. buffer-i-enzyme control (0.1 mmol/L sodium phosphate, lOmmol/L Na2-EDTA, 5 mmol/L DTT, 5% (v/v) glycerol, pH 8.

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