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
Quality Segment
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
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
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.
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
Certificates of Analysis (COA)
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