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737739

Sigma-Aldrich

Z-Ile-Bt

95%

Synonym(s):

(1S,2S-N-Z-1-Benzotriazolylcarbonyl-2-methylbutylamine, Benzyl (2S,3S)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate

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About This Item

Empirical Formula (Hill Notation):
C20H22N4O3
CAS Number:
Molecular Weight:
366.41
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.22

Product Name

Z-Ile-Bt, 95%

assay

95%

form

solid

mp

77-82 °C

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)OCc1ccccc1)C(=O)n2nnc3ccccc23

InChI

1S/C20H22N4O3/c1-3-14(2)18(21-20(26)27-13-15-9-5-4-6-10-15)19(25)24-17-12-8-7-11-16(17)22-23-24/h4-12,14,18H,3,13H2,1-2H3,(H,21,26)/t14-,18-/m0/s1

InChI key

DWJVZQUFTBRSCU-KSSFIOAISA-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[1]
  • Peptidomimetics, such as aminoxypeptides[2], depsipeptides[3] and heterocyclic peptidomimetics[4]
  • Tagged peptides and peptidomimetics, particularly those with fluorescent labels[5][6]
  • N, O, S, and C linked peptide conjugates[6]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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