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8.52418

Sigma-Aldrich

Fmoc-Asp(OBno)-OH

Novabiochem®

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Synonym(s):
Fmoc-Asp(OBno)-OH
Empirical Formula (Hill Notation):
C32H43NO6
Molecular Weight:
537.69

Quality Level

product line

Novabiochem®

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

carboxylic acid

storage temp.

−20°C (−15°C to −25°C)

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This Item
8.524018.524118.52183
Fmoc-Asp(OBno)-OH Novabiochem®

Sigma-Aldrich

8.52418

Fmoc-Asp(OBno)-OH

Fmoc-Asp(OEpe)-OH Novabiochem®

Sigma-Aldrich

8.52401

Fmoc-Asp(OEpe)-OH

Fmoc-Asn(Mmt)-OH Novabiochem®

Sigma-Aldrich

8.52411

Fmoc-Asn(Mmt)-OH

form

powder

form

powder

form

powder

form

powder

functional group

carboxylic acid

functional group

carboxylic acid

functional group

amide

functional group

hydroxyl

storage temp.

−20°C (−15°C to −25°C)

storage temp.

15-25°C

storage temp.

15-25°C

storage temp.

2-8°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

General description

An excellent derivative for minimizing aspartimide formation during Fmoc SPPS, including those containing the Asp-Gly sequence. The bulky OBno protecting group offers considerably more protection against the formation of aspartimide-related by-products than the commonly used OtBu and OMpe group.,

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Overcoming Aspartimide Formation in Fmoc SPPS

Literature references:
[1] R. Behrendt, et al. (2015) J. Pept. Sci., 21, 680.
[2] R. Behrendt, et al. (2016) J. Pept. Sci., 22, 92.

Application

Recently, Fmoc-Asp(OBno)-OH has been used in the synthesis of the mini-protein Omomyc, which has been shown to repress MYC-dependent gene transcription.,

Analysis Note

Color (visual): white to beige
Appearance of substance (visual): powder, chunks or crystals
Identity (IR): passes test
Purity (TLC (018A)): ≥ 95 %
Enantiomeric purity: ≥ 99.5 % (a/a)
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Multiple Synthetic Routes to the Mini-Protein Omomyc and Coiled-Coil Domain Truncations
Brown ZZ, et al.
The Journal of Organic Chemistry, 1466-1466 (2020)
Preventing aspartimide formation in Fmoc SPPS of Asp-Gly containing peptides?practical aspects of new trialkylcarbinol based protecting groups
R. Behrendt, et al.
Journal of Peptide Science, 22, 92-92 (2016)
Synthesis and evaluation of a multifunctional probe with a high affinity for prostate-specific membrane antigen (PSMA) and bone
Hirata S, et al.
Nuclear Medicine and Biology, 114-115, 34-41 (2022)
New t-butyl based aspartate protecting groups preventing aspartimide formation in Fmoc SPPS
R. Behrendt, et al.
Journal of Peptide Science, 21, 680-680 (2015)
Omomyc Reveals New Mechanisms To Inhibit the MYC Oncogene
Mark J. Demma, et al.
Molecular and Cellular Biology, 39 (2019)

Articles

Aspartimide formation 1,2 is caused by repeated exposure of aspartic acid-containing sequences to bases like piperidine and can result ultimately in the generation of 9 different by-products.

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