N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine

Name: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine
Brand: ChemScene
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CAS No. 749820-65-3
Cat. No. CS-0614292
Purity≥97%
MDL No.None

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine|CS-0614292

Structure of 749820-65-3

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General Information

CAS No. 749820-65-3
Cat. No. CS-0614292
Purity ≥97%
MDL No. None
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₇NO₇S
Molecular Weight 391.40
Synonym(s) None
SMILES O=C(O)[C@@H](CS(=O)(O)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O

Description

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine is a protected D-amino acid derivative featuring a fluorenylmethoxycarbonyl (Fmoc) group for orthogonal peptide synthesis and a sulfonate moiety at the C-terminal position. This combination enables site-specific incorporation into peptide sequences under standard coupling conditions, offering enhanced solubility and stability during synthetic workflows.

Application

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine serves as a protected D-alanine building block for peptide synthesis, leveraging the orthogonal stability of the Fmoc group and the sulfonate functionality for enhanced solubility. The sulfo group facilitates purification via ion-exchange chromatography and improves compatibility in aqueous environments. This derivative enables efficient incorporation of D-alanine into peptide sequences under standard coupling conditions, with robust bench stability and minimal side reactivity.

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-H319
Precautionary Statements : P264-P270-P280-P330-P501

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Computational Chemistry Data

TPSA 130
LogP 1.8661
H_Acceptors 5
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Sulfonic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-sulfo-D-alanine

CAS No. 749820-65-3

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