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8.52326

Sigma-Aldrich

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
UNSPSC Code:
12352209
NACRES:
NA.22

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

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

Related Categories

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

Regulatory Information

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Azido Acids in a Novel Method of Solid-Phase Peptide Synthesis.
M. Meldal, et al.
Tetrahedron Letters, 38, 2531-2531 (1997)

Articles

Selecting Orthogonal Building Blocks

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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