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8.52044

FMOC-Asn(Trt)-OH

Name: FMOC-Asn(Trt)-OH
Brand: MM

N-α-Fmoc-N-ß-trityl-L-asparagine Novabiochem^®

Synonym(s):

FMOC-Asn(Trt)-OH, N-α-Fmoc-N-β-trityl-L-asparagine

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About This Item

Empirical Formula (Hill Notation):

C₃₈H₃₂N₂O₅

CAS Number:

132388-59-1

Molecular Weight:

596.67

MDL number:

MFCD00077049

UNSPSC Code:

12352209

NACRES:

NA.22

Quality Level

400

product line

Novabiochem^®

Assay

≥98% (TLC)
≥98.0% (acidimetric)
≥99.0% (HPLC)

form

powder

potency

>2000 mg/kg LD₅₀, oral (Rat)

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem^®

mp

210-220 °C

solubility

<0.00005 g/L

application(s)

peptide synthesis

functional group

amide

storage temp.

−20°C (−15°C to −25°C)

InChI

1S/C38H32N2O5/c41-35(40-38(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28)24-34(36(42)43)39-37(44)45-25-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33/h1-23,33-34H,24-25H2,(H,39,44)(H,40,41)(H,42,43)/p-1/t34-/m0/s1

InChI key

KJYAFJQCGPUXJY-UMSFTDKQSA-M

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities.
Fmoc-Asn(Trt)-OH has good solubility properties in most organic solvents, and its use has been shown to result in significantly purer peptides than other derivatives used for the introduction of Asn ^[1,2]. Coupling can be performed by standard procedures. The trityl group is normally removed by 95% TFA in 1-3 hours, with no alkylation of Trp residues. When Asn(Trt) is the N-terminal residue, the reaction time may need to be extended to ensure complete deprotection ^[3].

Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] P. Sieber, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium′, R. Epton (Eds), SPCC UK Ltd., Birmingham, 1990, pp. 577.
^[2] P. Sieber, et al. (1991) Tetrahedron Lett., 32, 739.
^[3] M. Friede, et al. (1992) Pept. Res., 5, 145.

Application

Synthesis of a burkholdine analogue containing β-hydroxytyrosine: This study discusses the synthesis of a burkholdine analogue, utilizing Fmoc-Asn(Trt)-OH as part of the solid support loading process (Kato et al., 2019).

Linkage

Replaces: 04-12-1089

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.7 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Asn (Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Asn(Trt)-Asn(Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Asn-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (GC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (25 mmole in 50 ml DMF): clearly soluble
Assay (acidimetric): ≥ 98.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.05 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Legal Information

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

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Hazard Classifications

Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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