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8.52326

Fmoc-azidolysine

≥98.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-azidolysine

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About This Item

Empirical Formula (Hill Notation):
C21H22N4O4
CAS Number:
159610-89-6
Molecular Weight:
394.42
MDL number:
MFCD13182319
UNSPSC Code:
12352209
NACRES:
NA.22
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Product Name

Fmoc-azidolysine, Novabiochem®

Quality Level

200

product line

Novabiochem®

assay

≥98.0% (HPLC)

form

powder

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-])=NCCCC[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O

InChI

1S/C21H22N4O4/c22-25-23-12-6-5-11-19(20(26)27)24-21(28)29-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18-19H,5-6,11-13H2,(H,24,28)(H,26,27)/t19-/m0/s1

InChI key

PJRFTUILPGJJIO-IBGZPJMESA-N

General description

A useful tool for the synthesis of branched, side-chain modified and 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 or phosphines. ,

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.

Application

Recent applications of Fmoc-azidolysine include:
  • In the synthesis of a cationic cell-penetrating peptide (CPP) by click-chemistry.
  • In the preparation of a peptide-resorcinarene conjugate by click chemistry.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Articles

Selecting Orthogonal Building Blocks

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

Global Trade Item Number

SKUGTIN
852326000104027269237240
852326000504027269905637