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Merck
CN

737704

Sigma-Aldrich

Z-Trp-Bt

95%

Synonym(s):

(S)-N-Z-1-Benzotriazolylcarbonyl-2-(3-indolyl)ethylamine, (S)-Benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamate

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About This Item

Empirical Formula (Hill Notation):
C25H21N5O3
CAS Number:
850232-59-6
Molecular Weight:
439.47
MDL number:
MFCD06762898
UNSPSC Code:
12352202
PubChem Substance ID:
329765222

Key Documents

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Product Name

Z-Trp-Bt, 95%

Assay

95%

form

solid

mp

100-107 °C

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)n3nnc4ccccc34)OCc5ccccc5

InChI

1S/C25H21N5O3/c31-24(30-23-13-7-6-12-21(23)28-29-30)22(14-18-15-26-20-11-5-4-10-19(18)20)27-25(32)33-16-17-8-2-1-3-9-17/h1-13,15,22,26H,14,16H2,(H,27,32)/t22-/m0/s1

InChI key

OFKXDFXFJAJJHZ-QFIPXVFZSA-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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class Code

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
MKBJ1872V

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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)
Abdelmajeid, A.; Tala, S. R.; Amine, M. S.; Katritzky, A. R.
Synthesis, 2995-3005 (2011)
Katritzky, A. R.; Angrish, P.; Todadze, E.
Synlett, 2392-2411 (2009)
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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