Z-Pro-OH

Names

[ Name ]:
Z-Pro-OH

[Synonym ]:
(S)-N-(benzyloxycarbonyl)-proline
Cbz-L-proline
1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L-
EINECS 214-557-4
(S)-1-(benzyloxycarbonyl)-pyrrolidine-2-carboxylic acid
(S)-N-CBZ-pyrrolidine-2-carboxylic acid
N-Benzyloxycarbonyl-L-proline
N-Carbobenzyloxy-L-proline
(2S)-1-[(Phenylmethoxy)carbonyl]pyrrolidine-2-carboxylic acid
Carbobenzyloxy-L-proline
MFCD00003170
1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (2S)-
N-Carbobenzoxy-L-proline
(S)-1-carbobenzoxypyrrolidine-2-carboxylic acid
MFCD00020830
1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)-
Carbobenzoxy-L-proline
1-[(Benzyloxy)carbonyl]-L-proline
N-Cbz-L-proline
N-benzyloxycarbonyl-(S)-proline
(2S)-1-Phenylmethoxycarbonylpyrrolidine-2-carboxylicacid
Z-L-Proline
1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI)
Z-Pro-OH
N-[(phenyl-methoxy)carbonyl]-L-proline
Benzyloxycarbonyl-L-proline

Biological Activity

[Description]:

Carbobenzoxyproline (L-Cbz-Proline) is an inhibitor of prolidase. Carbobenzoxyproline can be used for prolidase deficiency (PD) research[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

Carbobenzoxyproline (6 mM; 0-10 d; pH=6.0) causes mitochondrial depolarization and increases cellular death by 33% as reported for long-term culture of fibroblasts from prolidase deficiency (PD) patients[1]. Carbobenzoxyproline (0, 1, 3, 6 mM; 1 min; pH=6.0) results fibroblasts prolidase (FBP) hydrolysis, shows linear competitive inhibition[1].

[In Vivo]

Carbobenzoxyproline (60 mg/kg; injection; once daily; 3 weeks) serves as in vivo inhibitor of erythrocytes prolidase in mice model[1]. Animal Model: C57Bl/6J mice (4-week-old)[1] Dosage: 60 mg/kg Administration: Injection; once daily for 3 weeks Result: Resulted significant reduction of erythrocytes prolidase activity.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
432.3±45.0 °C at 760 mmHg

[ Melting Point ]:
76-78ºC

[ Molecular Formula ]:
C₁₃H₁₅NO₄

[ Molecular Weight ]:
249.262

[ Flash Point ]:
215.3±28.7 °C

[ Exact Mass ]:
249.100113

[ PSA ]:
66.84000

[ LogP ]:
1.17

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.582

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY0745000

CHEMICAL NAME :: 1,2-Pyrrolidinedicarboxylic acid, 1-benzyl ester, L-

CAS REGISTRY NUMBER :: 1148-11-4

LAST UPDATED :: 199406

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C13-H15-N-O4

MOLECULAR WEIGHT :: 249.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravaginal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 280 mg/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 280 ug/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 68,696,1979

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R62

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UY0745000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Prolidase is required for early trafficking events during influenza A virus entry.

J. Virol. 88(19) , 11271-83, (2014)

Influenza A virus (IAV) entry is a multistep process that requires the interaction of the virus with numerous host factors. In this study, we demonstrate that prolidase (PEPD) is a cellular factor req...

N-benzyloxycarbonyl-L-proline: an in vitro and in vivo inhibitor of prolidase.

Biochim. Biophys. Acta 1744(2) , 157-63, (2005)

Prolidase deficiency (PD) is a recessive disorder of the connective tissue caused by mutations in the prolidase, a specific peptidase, cleaving the dipeptides with a C-terminal prolyl and hydroxyproly...

Proline prodrug of melphalan targeted to prolidase, a prodrug activating enzyme overexpressed in melanoma.

Pharm. Res. 24(7) , 1290-8, (2007)

To determine the bioactivation and uptake of prolidase-targeted proline prodrugs of melphalan in six cancer cell lines with variable prolidase expression and to evaluate prolidase-dependence of prodru...

Related Compounds

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