Fmoc-Asn(Trt)-OH (CAS 132388-59-1), also known as Nα-Fmoc-Nγ-trityl-L-asparagine, is a doubly protected asparagine derivative for Fmoc-SPPS. It belongs to the Fmoc-Asn-triphenylmethyl class. To stop dehydration to Asp-nitrile during activation reactions and to stop the formation of aspartimide (succinimide) side products during synthesis, the primary amide side chain of asparagine needs to be protected (Trt group). During global deprotection, TFA (with scavengers like triisopropylsilane) removes the Trt group. Asparagine is especially likely to turn into aspartimide when Fmoc-SPPS is done on certain sequences (Asn-Gly, Asn-Ala motifs); Trt protection stops this from happening. Deamidation (Asn→Asp) is a major way that these peptides break down and a source of process impurity.
ApiSyn sells Fmoc-Asn(Trt)-OH (CAS 132388-59-1) as a pharmaceutical-grade Fmoc amino acid building block and an important raw material reference standard for GMP peptide SPPS and quality control.
| Chemical Name | N2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N4-trityl-L-asparagine |
| Molecular Formula | C38H32N2O5 |
| Molecular Weight | 596.7 |
| CAS Number | 132388-59-1 |