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About This Item
Linear Formula:
C6H5CH2OOCNHCH2COOH
CAS Number:
Molecular Weight:
209.20
Beilstein:
526877
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
99%
form
powder
reaction suitability
reaction type: solution phase peptide synthesis
color
beige
mp
118-122 °C (lit.)
application(s)
peptide synthesis
SMILES string
OC(=O)CNC(=O)OCc1ccccc1
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)
InChI key
CJUMAFVKTCBCJK-UHFFFAOYSA-N
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General description
Z-Gly-OH, also known as N-benzyloxycarbonylglycine, is an amino acid widely used in solution phase peptide synthesis.
Application
Z-Gly-OH is a versatile reagent that can be used to synthesize a variety of compounds such as:
- glycine-derived peptides like Z-Gly-DL-Ala-OBzl and Z-Gly-L-Ala-OBzl
- glycine N-substituted amides such as glycine-N-methylamide hydrochloride and glycine-N-isopropylamide hydrochloride
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Formation of peptide bonds in the coordination sphere of cobalt (III)
Journal of the American Chemical Society, 89, 6096-6103 (1967)
Studies on Separation of Amino Acids and Related Compounds. V. A Racemization Test in Peptide Synthesis by the Use of an Amino Acid Analyzer
Bulletin of the Chemical Society of Japan, 44, 3391-3395 (1971)
Duality of mechanism in the tetramethylfluoroformamidinium hexafluorophosphate-mediated synthesis of N-benzyloxycarbonylamino acid fluorides.
R Fiammengo et al.
The Journal of organic chemistry, 66(17), 5905-5910 (2001-08-21)
G K Scriba et al.
The Journal of pharmacy and pharmacology, 51(5), 549-553 (1999-07-20)
Glycine, which has weak anticonvulsant properties, has been shown to potentiate the activity of several antiepileptic drugs but not phenytoin. Recently, studies have shown that N-(benzyloxycarbonyl)glycine (Z-glycine) antagonized seizures more than glycine in addition to possessing activity in the maximal
D M Lambert et al.
Neuroreport, 5(7), 777-780 (1994-03-21)
Although glycine does not cross easily the blood-brain barrier, it exhibits at very high doses (10-40 mmol kg-1) a modest anticonvulsant 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
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