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8.52326

Sigma-Aldrich

Fmoc-azidolysine

Novabiochem®

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Synonym(s):
Fmoc-azidolysine
Empirical Formula (Hill Notation):
C21H22N4O4
CAS Number:
Molecular Weight:
394.42

Quality Level

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

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

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8.523228.523218.52352
Fmoc-azidolysine Novabiochem®

Sigma-Aldrich

8.52326

Fmoc-azidolysine

assay

≥98.0% (HPLC)

assay

≥95.0% (HPLC)

assay

-

assay

≥98.0% (HPLC)

form

powder

form

powder

form

solid

form

powder

functional group

azide

functional group

azide

functional group

azide

functional group

azide

storage temp.

15-25°C

storage temp.

15-25°C

storage temp.

15-25°C

storage temp.

15-25°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Azido Acids in a Novel Method of Solid-Phase Peptide Synthesis.
M. Meldal, et al.
Tetrahedron Letters, 38, 2531-2531 (1997)
Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids
J. T. Lundquist & J. C. Pelletier
Organic Letters, 3, 781-781 (2001)
Switch peptide via Staudinger reaction
N. Nepomniaschiy, et al.
Organic Letters, 10, 5243-5243 (2008)
Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity
Pineda-Castaneda H, et al.
Antibiotics, 12, 773-773 (2023)
Cyclization of a cell-penetrating peptide via click-chemistry increases proteolytic resistance and improves drug delivery
Reichart F, et al.
Journal of Peptide Science, 22, 421-426 (2016)

Articles

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications.

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

Contact Technical Service