Synonym
Carbobenzoxyphenylalanine; Carbobenzoxy-L-phenylalanine; NSC 402059; NSC-402059; NSC402059; Z-Phe-OH; Z-L-Phenylalanine; Cbz-Phe-OH N-Cbz-L-phenylalanine;
IUPAC/Chemical Name
((benzyloxy)carbonyl)-L-phenylalanine
InChi Key
RRONHWAVOYADJL-HNNXBMFYSA-N
InChi Code
InChI=1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1
SMILES Code
O=C(O)[C@H](CC1=CC=CC=C1)NC(OCC2=CC=CC=C2)=O
Purity
>95% (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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
299.32
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 |
1: Carter DB, Chae CB. Chromatin-bound protease: degradation of chromosomal proteins under chromatin dissociation conditions. Biochemistry. 1976 Jan 13;15(1):180-5. PubMed PMID: 2280.
2: Jany KD, Haug H, Pfleiderer G, Ishay J. Enzymatic and chemical properties of an endopeptidase from the larva of the hornet Vespa crabro. Biochemistry. 1978 Oct 31;17(22):4675-82. PubMed PMID: 103567.
3: Ceruso M, Howe N, Malthouse JP. Mechanism of the binding of Z-L-tryptophan and Z-L-phenylalanine to thermolysin and stromelysin-1 in aqueous solutions. Biochim Biophys Acta. 2012 Feb;1824(2):303-10. doi: 10.1016/j.bbapap.2011.10.007. Epub 2011 Oct 19. PubMed PMID: 22037182.
4: Wiese J, Gattner HG, Zahn H. Use of Z-amino acid-glyceryl esters in protease catalyzed peptide synthesis. Biomed Biochim Acta. 1991;50(10-11):S90-3. PubMed PMID: 1820068.
5: Stoeva S. Modification of a zinc proteinase from Bacillus mesentericus strain 76 by diethylpyrocarbonate. Int J Pept Protein Res. 1991 Apr;37(4):325-30. PubMed PMID: 1894447.
6: Mitić D, Milenković M, Milosavljević S, Godevac D, Miodragović Z, Andelković K, Miodragović D. Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine. Eur J Med Chem. 2009 Apr;44(4):1537-44. doi: 10.1016/j.ejmech.2008.07.017. Epub 2008 Jul 23. PubMed PMID: 18760509.
7: Harris B, Cheek TR, Burgoyne RD. Effects of metalloendoproteinase inhibitors on secretion and intracellular free calcium in bovine adrenal chromaffin cells. Biochim Biophys Acta. 1986 Oct 31;889(1):1-5. PubMed PMID: 3533161.
8: Shieh TL, Byrn SR. Solution conformation of the thermolysin inhibitors carbobenzoxy-L-phenylalanine and beta-phenylpropionyl-L-phenylalanine and comparison of the solution conformation to the enzyme-bound conformation. J Med Chem. 1982 Apr;25(4):403-8. PubMed PMID: 7069718.
9: Rusu I, Yaron A. Aminopeptidase P from human leukocytes. Eur J Biochem. 1992 Nov 15;210(1):93-100. PubMed PMID: 1446689.