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C7206

Sigma-Aldrich

Z-Gly-OH

99%

Synonym(s):

Z-Glycine

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¥5,760
100 G
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25 G
¥5,760
100 G
¥20,200
500 G
¥42,700

About This Item

Linear Formula:
C6H5CH2OOCNHCH2COOH
CAS Number:
1138-80-3
Molecular Weight:
209.20
Beilstein:
526877
EC Number:
214-516-0
MDL number:
MFCD00002691
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24892944
NACRES:
NA.22

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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[1]
  • glycine N-substituted amides such as glycine-N-methylamide hydrochloride and glycine-N-isopropylamide hydrochloride[2]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

C7206-VAR:
C7206-500G:
C7206-25G:
C7206-100G:
C7206-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2811
SDBB2120
SDBB0270
STBL0631
STBK8384

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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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