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C7206

Sigma-Aldrich

Z-Gly-OH

99%

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Synonym(s):
Z-Glycine
Linear Formula:
C6H5CH2OOCNHCH2COOH
CAS Number:
Molecular Weight:
209.20
Beilstein/REAXYS Number:
526877
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
G10029684015420
Z-Gly-OH 99%

C7206

Z-Gly-OH

Gly-Gly ≥99% (titration)

G1002

Gly-Gly

H-Lys(Z)-OH ≥99.0% (NT)

96840

H-Lys(Z)-OH

Boc-Gly-OH ≥99.0% (T)

15420

Boc-Gly-OH

assay

99%

assay

≥99% (titration)

assay

≥99.0% (NT)

assay

≥99.0% (T)

mp

118-122 °C (lit.)

mp

262-264 °C

mp

259 °C (dec.) (lit.)

mp

86-89 °C (lit.)

color

beige

color

white

color

-

color

-

Quality Level

200

Quality Level

400

Quality Level

-

Quality Level

-

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

-

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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
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)
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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