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737712

Sigma-Aldrich

Z-Phe-Bt

Synonym(s):

(S)-N-Z-1-Benzotriazolylcarbonyl-2-phenylethylamine, (S)-Benzyl 1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

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About This Item

Empirical Formula (Hill Notation):
C23H20N4O3
CAS Number:
769922-77-2
Molecular Weight:
400.43
MDL number:
MFCD22200497
UNSPSC Code:
12352202
PubChem Substance ID:
329765223
NACRES:
NA.22

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

143-150 °C

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

O=C(N[C@@H](Cc1ccccc1)C(=O)n2nnc3ccccc23)OCc4ccccc4

InChI

1S/C23H20N4O3/c28-22(27-21-14-8-7-13-19(21)25-26-27)20(15-17-9-3-1-4-10-17)24-23(29)30-16-18-11-5-2-6-12-18/h1-14,20H,15-16H2,(H,24,29)/t20-/m0/s1

InChI key

YKOJLKRZEWWYIH-FQEVSTJZSA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ1873V

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Katritzky, A. R.; Narindoshvili, T.; Angrish, P.
Synthesis, 2013-2022 (2008)
Hansen, F. K.; Beagle, L. K.; Todadze, E.; Katritzky, A. R.
Heterocycles, 515-526 (2012)
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
Katritzky, A. R.; Angrish, P.; Todadze, E.
Synlett, 2392-2411 (2009)
Abdelmajeid, A.; Tala, S. R.; Amine, M. S.; Katritzky, A. R.
Synthesis, 2995-3005 (2011)
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