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Merck
CN

737712

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
NACRES:
NA.22
PubChem Substance ID:
329765223
UNSPSC Code:
12352202
MDL number:
MFCD22200497

Key Documents

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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

SMILES string

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

InChI key

YKOJLKRZEWWYIH-FQEVSTJZSA-N

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

143-150 °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
MKBJ1873V

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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)
Alan R Katritzky et al.
The Journal of organic chemistry, 74(22), 8690-8694 (2009-10-17)
N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e'), and (3g+3g'), aminoxy hybrid peptides 4a-h, (4a+4a'), 6a-d, 9a-e, (9a+9a'), and (9b+9b'), and alpha-aminoxy
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