Synonym
N-Benzyloxycarbonylglycine; Carbobenzoxyglycine; N-Carbobenzoxyglycine
IUPAC/Chemical Name
N-Carbobenzoxyglycine
InChi Key
CJUMAFVKTCBCJK-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H11NO4/c12-9(13)6-11-10(14)15-7-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,14)(H,12,13)
SMILES Code
c1(COC(NCC(O)=O)=O)ccccc1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Z-Glycine is a Glycine (HY-Y0966) derivative.
In vivo activity:
In this study, carbamate derivatives--N-benzyloxycarbonylglycine (Z-glycine) and N,tert-butoxycarbonylglycine (Boc-glycine)--have been compared with glycine. Z-glycine (1 mmol kg-1), but not Boc-glycine, reduces the number of tonic convulsions in the 3-mercaptopropionic and in the bicuculline tests, increases the latency of seizures in the strychnine test and is as active 3 h after administration as sodium valproate 30 min after administration in the maximal electroshock seizure test. Overall, milacemide, a precursor of glycine, and Z-glycine have rather similar anticonvulsant profiles in mice.
Reference: Neuroreport. 1994 Mar 21;5(7):777-80. https://pubmed.ncbi.nlm.nih.gov/8018849/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
209.20
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
Lambert DM, Poupaert JH, Maloteaux JM, Dumont P. Anticonvulsant activities of N-benzyloxycarbonylglycine after parenteral administration. Neuroreport. 1994 Mar 21;5(7):777-80. doi: 10.1097/00001756-199403000-00010. PMID: 8018849.
In vivo protocol:
Lambert DM, Poupaert JH, Maloteaux JM, Dumont P. Anticonvulsant activities of N-benzyloxycarbonylglycine after parenteral administration. Neuroreport. 1994 Mar 21;5(7):777-80. doi: 10.1097/00001756-199403000-00010. PMID: 8018849.
1: Fiammengo R, Licini G, Nicotra A, Modena G, Pasquato L, Scrimin P, Broxterman QB, Kaptein B. Duality of mechanism in the tetramethylfluoroformamidinium hexafluorophosphate-mediated synthesis of N-benzyloxycarbonylamino acid fluorides. J Org Chem. 2001 Aug 24;66(17):5905-10. PubMed PMID: 11511270.
2: Lambert DM. Rationale and applications of lipids as prodrug carriers. Eur J Pharm Sci. 2000 Oct;11 Suppl 2:S15-27. Review. PubMed PMID: 11033424.
3: Scriba GK, Lambert DM. Synthesis and anticonvulsant activity of N-benzyloxycarbonyl-amino acid prodrugs of phenytoin. J Pharm Pharmacol. 1999 May;51(5):549-53. PubMed PMID: 10411214.
4: Sussan S, Dagan A, Bialer M. Pharmacokinetic analysis and anticonvulsant activity of glycine and glycinamide derivatives. Epilepsy Res. 1999 Jan;33(1):11-21. PubMed PMID: 10022362.
5: Lambert DM, Geurts M, Scriba GK, Poupaert JH, Dumont P. [Simple derivatives of amino acid neurotransmitters. Anticonvulsant evaluation of derived amides, carbamates and esters of glycine and beta-alanine]. J Pharm Belg. 1995 Mar-Jun;50(2-3):194-203. French. PubMed PMID: 7674119.
6: Lambert DM. [Simple glycine derivatives from lipid transporter systems of glycine. Carrier test of a small-size neutral acid amine to the central nervous system]. Bull Mem Acad R Med Belg. 1995;150(7-9):294-300. French. PubMed PMID: 8688842.
7: Lambert DM, Poupaert JH, Maloteaux JM, Dumont P. Anticonvulsant activities of N-benzyloxycarbonylglycine after parenteral administration. Neuroreport. 1994 Mar 21;5(7):777-80. PubMed PMID: 8018849.
8: Bundgaard H, Rasmussen GJ. Prodrugs of peptides. 11. Chemical and enzymatic hydrolysis kinetics of N-acyloxymethyl derivatives of a peptide-like bond. Pharm Res. 1991 Oct;8(10):1238-42. PubMed PMID: 1796040.
9: Ascenzi P, Aducci P, Torroni A, Amiconi G, Ballio A, Menegatti E, Guarneri M. The pH dependence of pre-steady-state and steady-state kinetics for the papain-catalyzed hydrolysis of N-alpha-carbobenzoxyglycine p-nitrophenyl ester. Biochim Biophys Acta. 1987 Apr 8;912(2):203-10. PubMed PMID: 3828360.
10: Schack P, Kaarsholm NC. Subsite differences between the active centres of papaya peptidase A and papain as revealed by affinity chromatography. Purification of papaya peptidase A by ionic-strength-dependent affinity adsorption on an immobilized peptide inhibitor of papain. Biochem J. 1984 May 1;219(3):727-33. PubMed PMID: 6378179; PubMed Central PMCID: PMC1153538.
11: Szawelski RJ, Wharton CW. Kinetic solvent isotope effects on the deacylation of specific acyl-papains. Proton inventory studies on the papain-catalysed hydrolyses of specific ester substrates: analysis of possible transition state structures. Biochem J. 1981 Dec 1;199(3):681-92. PubMed PMID: 6280675; PubMed Central PMCID: PMC1163425.
12: Yuthavong Y, Suttimool W. Rate constants of individual steps in papain-catalysed reactions. Biochim Biophys Acta. 1978 Mar 14;523(1):198-206. PubMed PMID: 629988.
13: Lowe G, Whitworth AS. A kinetic and fluorimetric investigation of papain modified at tryptophan-69 and -177 by N-bromosuccinimide. Biochem J. 1974 Aug;141(2):503-15. PubMed PMID: 4455219; PubMed Central PMCID: PMC1168105.
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