Ac-Asn(Trt)-OH

Ac-Asn(Trt)-OH is an N-acetylated, side-chain-protected asparagine derivative in which the asparagine side chain bears a trityl (Trt) protecting group and the molecule is presented as a carboxylic acid (-COOH). It contains an N-acetyl amide at the α-amino position and retains the α-carboxyl group, while the Trt group masks the side-chain amide functionality to control chemoselectivity and suppress undesired side reactions during peptide assembly. As a protected amino acid building block, Ac-Asn(Trt)-OH is used in stepwise synthesis of peptides and peptide analogues where orthogonal deprotection and selective coupling of the amino acid residue are required.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP26454

CAS No:163277-78-9

Synonyms/Alias:AC-ASN(TRT)-OH;163277-78-9;Nalpha-Acetyl-Ngamma-trityl-L-asparagine;AC1OLR7Q;CTK8E6095;ZINC4899633;6077AH;AKOS015909213;RT-014643;K-5101;(2S)-2-acetamido-4-oxo-4-(tritylamino)butanoicacid;I14-33142

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cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C25H24N2O4
M.W/Mr.
416.48

Ac-Asn(Trt)-OH is an N-acetylated asparagine derivative bearing a Trt (trityl) side-chain protecting group, supplied as a peptide-ready amino acid building block in the acid form. The N-acetyl group helps define the peptide N-terminus during segment coupling, while the Trt-protected side-chain amide is designed to remain stable under common peptide assembly conditions. This combination makes Ac-Asn(Trt)-OH well aligned with protected-peptide intermediate workflows where controlled reactivity and minimized side reactions are required.

1. Peptide Segment Coupling

Ac-Asn(Trt)-OH is used as a defined asparagine-containing segment building block in custom peptide synthesis, particularly when an N-acetylated residue is needed to match a target peptide's N-terminus or to standardize fragment junctions. Peptide chemists select this protected Asn derivative to carry the side-chain amide through assembly without premature side-chain participation, supporting reliable fragment condensation and downstream purification of peptide intermediates. The Trt protection pattern is commonly leveraged to balance side-chain stability with practical deprotection strategies during final peptide processing.

2. N-Acetylated Asparagine Intermediates

Ac-Asn(Trt)-OH supports the preparation of N-acetylated peptide intermediates used in iterative fragment assembly and late-stage coupling workflows. Researchers in peptide and protein chemistry often incorporate N-acetylation at the residue level to reproduce specific peptide architectures encountered in biochemical studies, including acetylated termini and acetylated internal motifs. By providing a pre-acetylated, side-chain-protected asparagine unit, this reagent streamlines intermediate design where consistent protection and controlled deprotection behavior are important for maintaining sequence integrity.

3. Complex Peptide Synthesis

Ac-Asn(Trt)-OH is applied in the synthesis of longer or more structurally demanding peptides where minimizing undesired reactivity during coupling steps is a practical priority. Peptide development teams use Trt-protected asparagine building blocks to reduce the risk of side reactions associated with unprotected side-chain functionality while building sequence complexity across multiple coupling cycles. This makes Ac-Asn(Trt)-OH particularly relevant for preparing protected peptide fragments that must survive purification and handling before final global deprotection and conversion to the target peptide.

Size
1 g;5 g;
InChI
1S/C25H24N2O4/c1-18(28)26-22(24(30)31)17-23(29)27-25(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-16,22H,17H2,1H3,(H,26,28)(H,27,29)(H,30,31)/t22-/m0/s1
InChI Key
IDBQTOJMHIZVEK-QFIPXVFZSA-N
Canonical SMILES
CC(=O)NC(CC(=O)NC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O

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