1-[(1,1-Dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine

Name: 1-[(1,1-Dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine
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CAS No. 159631-28-4
Cat. No. CS-0447559
Purity≥96%
MDL No.MFCD00151927

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1-[(1,1-Dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine|CS-0447559

Structure of 159631-28-4

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General Information

CAS No. 159631-28-4
Cat. No. CS-0447559
Purity ≥96%
MDL No. MFCD00151927
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₇N₃O₆
Molecular Weight 477.51
Synonym(s) Fmoc-D-His(Boc)-OH
SMILES CC(C)(OC(N1C=C(N=C1)C[C@@H](NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O)C(O)=O)=O)C

Description

This fluorenylmethoxycarbonyl-protected D-histidine derivative features orthogonal functional groups enabling selective peptide coupling. The tert-butyloxycarbonyl and fluorenylmethoxycarbonyl moieties provide robust protection for amine and imidazole side chain, respectively, under standard conditions. Designed for efficient incorporation into synthetic peptides with minimal epimerization.

Application

Boc-Fmoc-D-His-OH serves as a key chiral building block for peptide synthesis, enabling sequential coupling in solid-phase and solution-phase workflows. The Boc group provides reliable protection of the α-amino function, while the Fmoc moiety offers orthogonal deprotection under mild basic conditions. The D-histidine side chain maintains native imidazole functionality, facilitating incorporation into bioactive peptides and heterocyclic scaffolds with minimal steric perturbation. Exhibits excellent bench stability and compatibility with standard purification methods.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 119.75
LogP 4.2007
H_Acceptors 7
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Histidine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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1-[(1,1-Dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-histidine

CAS No. 159631-28-4

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