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8.52351

cis-Fmoc-Pro(4-N3)-OH

Name: cis-Fmoc-Pro(4-N3)-OH
Brand: MM

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

Synonym(s):

cis-Fmoc-Pro(4-N3)-OH, Fmoc-(2S, 4S)-4-azidoproline

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₁₈N₄O₄

CAS Number:

263847-08-1

Molecular Weight:

378.38

MDL number:

MFCD04115792

UNSPSC Code:

12352209

NACRES:

NA.22

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Properties

Product Name

cis-Fmoc-Pro(4-N3)-OH, Novabiochem^®

Quality Segment

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-])=N[C@@H]1CN([C@@H](C1)C(=O)O)C(=O)OCC2c3c(cccc3)c4c2cccc4

InChI

1S/C20H18N4O4/c21-23-22-12-9-18(19(25)26)24(10-12)20(27)28-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,25,26)/t12-,18-/m0/s1

InChI key

HOPXMBBEYJTPNX-SGTLLEGYSA-N

Description

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
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.

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 3

flash_point_f

Not applicable

flash_point_c