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Merck
CN

737747

Sigma-Aldrich

z-ala-bt

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H16N4O3
CAS Number:
Molecular Weight:
324.33
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

95-100 °C

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

C[C@H](NC(OCC1=CC=CC=C1)=O)C(N(N=N2)C3=C2C=CC=C3)=O

InChI

1S/C17H16N4O3/c1-12(18-17(23)24-11-13-7-3-2-4-8-13)16(22)21-15-10-6-5-9-14(15)19-20-21/h2-10,12H,11H2,1H3,(H,18,23)/t12-/m0/s1

InChI key

LREHLGSLFLKDDH-LBPRGKRZSA-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

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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Katritzky, A. R.; et al.
Synlett, 2392-2411 (2009)
Avan, I.; et al.
The Journal of Organic Chemistry, 4884-4893 null
Abdelmajeid, A.; et al.
Synthesis, 2995-3005 (2011)
Katritzky, A. R.; et al.
The Journal of Organic Chemistry, 8690-8694 (2009)
Hansen, F. K.; et al.
Heterocycles, 515-526 (2012)

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