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Merck
CN

8.52321

Fmoc-γ-azidohomoalanine

Novabiochem®

Synonym(s):

Fmoc-γ-azidohomoalanine

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About This Item

Empirical Formula (Hill Notation):
C19H18N4O4
CAS Number:
Molecular Weight:
366.37
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22
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Product Name

Fmoc-γ-azidohomoalanine, Novabiochem®

SMILES string

[N+](=[N-])=NCC[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O

InChI

1S/C19H18N4O4/c20-23-21-10-9-17(18(24)25)22-19(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H,22,26)(H,24,25)/t17-/m0/s1

InChI key

CLEZARXVEABQBI-KRWDZBQOSA-N

product line

Novabiochem®

form

solid

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

azide

storage temp.

15-25°C

Quality Level

General description

A useful tool for the synthesis of branched, side-chain modified, cyclic peptides and peptide tools for click chemistry by Fmoc SPPS. The side-chain azido group is completely stable to piperidine and TFA, but can be readily converted to an amine on the solid phase or in solution by reduction with thiols [1] or phosphines [2,3].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Guide to Selection of Orthogonally -Protected Building Blocks for Fmoc SPPS

Literature references

[1] M. Meldal, et al. (1997) Tetrahedron Lett., 38, 2531.
[2] J. T. Lundquist & J. C. Pelletier (2001) Org. Lett., 3, 781.
[3] N. Nepomniaschiy, et al. (2008) Org. Lett., 10, 5243.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Articles

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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