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Merck
CN

737801

Sigma-Aldrich

Fmoc-Gly-Bt

97%

Synonym(s):

9H-Fluoren-9-yl)methyl 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethylcarbamate, N-Fmoc-(1-benzotriazolylcarbonyl)methylamine

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About This Item

Empirical Formula (Hill Notation):
C23H18N4O3
CAS Number:
1082989-49-8
Molecular Weight:
398.41
MDL number:
MFCD11850150
UNSPSC Code:
12352202
PubChem Substance ID:
329765230
NACRES:
NA.26

Key Documents

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Assay

97%

form

solid

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

mp

160-168 °C

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

SMILES string

O=C(NCC(=O)n1nnc2ccccc12)OCC3c4ccccc4-c5ccccc35

InChI

1S/C23H18N4O3/c28-22(27-21-12-6-5-11-20(21)25-26-27)13-24-23(29)30-14-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-12,19H,13-14H2,(H,24,29)

InChI key

FKDIZKBMJXDKNM-UHFFFAOYSA-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

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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
MKBJ1865V

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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)
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)
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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