N-Fmoc-N-trityl-D-asparagine, CAS No. 180570-71-2

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180570-71-2

Catalog No. EBD51384

CAS 180570-71-2

Name N-Fmoc-N-trityl-D-asparagine

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Basic Information

Synonyms: N-Fmoc-N-trityl-D-asparagine N-(9-Fluorenylmethyloxycarbonyl)-N'-trityl-D-asparagine N-Fmoc-N'-trityl-D-asparagine n-alpha-fmoc-n-beta-trityl-d-asparagine n-alpha-9-fluorenylmethoxycarbonyl-n-omega-trityl-d-asparagine n-alpha-(9-fluorenylmethoxycarbonyl)-n-beta-trityl-d-asparagine n-alpha-(9-fluorenylmethyloxycarbonyl)-n-beta-trityl-d-asparagine fmoc-d-asn(trt) fmoc-d-asparagine(trityl) fmoc-d-asparagine(trt)

Molecular Formula: C38H32N2O5

Molecular Weight: 596.67

MDL Number: MFCD00151919

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

N-Fmoc-N-trityl-D-asparagine is a protected derivative of the amino acid D-asparagine. It features two orthogonal protecting groups: the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group on the α-amino function and the acid-labile trityl (Trt) group on the side-chain amide nitrogen. This specific protection scheme is crucial for its primary application. This compound is a fundamental building block in solid-phase peptide synthesis (SPPS) employing the Fmoc/tBu strategy. The D-asparagine side chain amide is prone to side reactions, such as dehydration to form a nitrile during peptide coupling or cleavage steps. The bulky trityl group effectively shields the β-carboxamide, preventing these undesired transformations and ensuring high-fidelity incorporation of D-asparagine into peptide sequences. It is therefore an essential specialty reagent for the synthesis of peptides containing this residue, particularly in research and development of therapeutic peptides and peptidomimetics. As a protected amino acid derivative, it serves as a key chiral synthon. Its well-defined stereochemistry (D-configuration) and orthogonal protecting groups make it valuable not only in peptide chemistry but also in the synthesis of more complex organic molecules and bioactive compounds where the asparagine moiety is required.

Physical Properties

Melting Point: 211-216 °C

Boiling Point: 831.397 °C at 760 mmHg

Flash Point: 456.613 °C

Density: 1.29 g/cm3

Storage: 2-8°C