(S)-2-(2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanoic acid

Name: (S)-2-(2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanoic acid
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CAS No. 2061897-68-3
Cat. No. CS-0162100
Molecule weight582.69
Purity≥97%
MDL No.MFCD32173661

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(S)-2-(2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanoic acid|CS-0162100

Structure of 2061897-68-3

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General Information

CAS No. 2061897-68-3
Cat. No. CS-0162100
Purity ≥97%
MDL No. MFCD32173661
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₄H₃₈N₄O₅
Molecular Weight 582.69
Synonym(s) Boc-his(trt)-aib-oh
SMILES CC(C)(NC([C@@H](NC(OC(C)(C)C)=O)CC1=CN(C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C=N1)=O)C(O)=O

Description

This protected amino acid derivative features a trityl-masked imidazole handle for orthogonal functionalization. The tert-butyl carbamate group enables selective deprotection, while the sterically hindered branched chain ensures stability during peptide coupling workflows. Designed for efficient incorporation into complex peptide architectures under standard conditions.

Application

(S)-2-(2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanoic acid serves as a versatile building block for the synthesis of imidazole-containing peptide mimetics and constrained peptidomimetic scaffolds. The trityl group provides robust protection for the imidazole nitrogen, enabling orthogonal deprotection during solid-phase synthesis. The tert-butyl carbamate moiety offers excellent stability under standard peptide coupling conditions, while the branched aliphatic backbone enhances conformational rigidity and metabolic stability—ideal for medicinal chemistry applications requiring precise spatial orientation and enhanced bioavailability.

Safety Information

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Computational Chemistry Data

TPSA 122.55
LogP 5.1385
H_Acceptors 6
H_Donors 3
Rotatable_Bonds 10

Other Classifications

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-(2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-2-methylpropanoic acid

CAS No. 2061897-68-3

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