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Merck
CN

737763

Fmoc-Pro-Bt

0.95

Synonym(s):

(S)-(9H-Fluoren-9-yl)methyl 2-(1H-benzo[d][1,2,3]triazole-1-carbonyl)pyrrolidine-1-carboxylate, (S)-N-Fmoc-2-(benzotriazolylcarbonyl)pyrrolidine

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About This Item

Empirical Formula (Hill Notation):
C26H22N4O3
CAS Number:
1155875-68-5
Molecular Weight:
438.48
MDL number:
MFCD11850301
UNSPSC Code:
12352209
PubChem Substance ID:
329765227
NACRES:
NA.26

Key Documents

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Product Name

Fmoc-Pro-Bt, 95%

Assay

95%

form

solid

mp

163-168 °C

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

O=C(OCC1c2ccccc2-c3ccccc13)N4CCC[C@H]4C(=O)n5nnc6ccccc56

InChI

1S/C26H22N4O3/c31-25(30-23-13-6-5-12-22(23)27-28-30)24-14-7-15-29(24)26(32)33-16-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-6,8-13,21,24H,7,14-16H2/t24-/m0/s1

InChI key

ZTDUGEKWIJHWKX-DEOSSOPVSA-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
MKBH1866V

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Katritzky, A. R.; Angrish, P.; Todadze, E.
Synlett, 2392-2411 (2009)
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)
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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