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Merck
CN

737720

Z-Gly-Bt

97%

Synonym(s):

N-Z-(1-Benzotriazolylcarbonyl)methylamine, Benzyl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethylcarbamate

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About This Item

Empirical Formula (Hill Notation):
C16H14N4O3
CAS Number:
173459-80-8
Molecular Weight:
310.31
NACRES:
NA.22
PubChem Substance ID:
329765224
UNSPSC Code:
12352202
MDL number:
MFCD06637948

Key Documents

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InChI

1S/C16H14N4O3/c21-15(20-14-9-5-4-8-13(14)18-19-20)10-17-16(22)23-11-12-6-2-1-3-7-12/h1-9H,10-11H2,(H,17,22)

SMILES string

O=C(NCC(=O)n1nnc2ccccc12)OCc3ccccc3

InChI key

GXIYFGDLDAFXEF-UHFFFAOYSA-N

assay

97%

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

110-117 °C

application(s)

peptide synthesis

storage temp.

−20°C

Application

Benzotriazole amino acids, or aminoacylbenzotriazolides, are versatile reagents for synthesizing peptides as well as their mimetics and conjugates. Benzotriazole amino acids have been used for the preparation of diverse derivatives including:

  • Polypeptidal benzotriazolides
  • Peptidomimetics, such as aminoxypeptides, depsipeptides and heterocyclic peptidomimetics
  • Tagged peptides and peptidomimetics, particularly those with fluorescent labels
  • N, O, S, and C linked peptide conjugates

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ1866V

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Katritzky, A. R.; Narindoshvili, T.; Angrish, P.
Synthesis, 2013-2022 (2008)
Katritzky, A. R.; Angrish, P.; Todadze, E.
Synlett, 2392-2411 (2009)
Hansen, F. K.; Beagle, L. K.; Todadze, E.; Katritzky, A. R.
Heterocycles, 515-526 (2012)
Abdelmajeid, A.; Tala, S. R.; Amine, M. S.; Katritzky, A. R.
Synthesis, 2995-3005 (2011)
Ilker Avan et al.
The Journal of organic chemistry, 76(12), 4884-4893 (2011-04-02)
Reactions of O-Pg(α-hydroxyacyl)benzotriazoles with (a) unprotected α-hydroxycarboxylic acids, (b) amino acids, and (c) amines afforded, respectively, chirally pure (a) oligoesters, (b) depsidipeptides, and (c) amide conjugates (yields 52-94%). N-Pg(α-Aminoacyl)benzotriazoles reacted with α-hydroxycarboxylic acids to yield depsidipeptides (47-87%). N-Pg(depsidipeptidoyl)benzotriazoles, obtained from
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