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532290

Sigma-Aldrich

2-Chlorotrityl chloride, polymer-bound

200-400 mesh, extent of labeling: 1.0-1.5 mmol/g Cl loading, 1 % cross-linked

Synonym(s):

2,α-Dichlorobenzhydryl-polystyrene crosslinked with divinylbenzene

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About This Item

CAS Number:
Beilstein:
1983914
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

Quality Level

crosslinking

1 % cross-linked

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

extent of labeling

1.0-1.5 mmol/g Cl loading

particle size

200-400 mesh

application(s)

peptide synthesis

SMILES string

Clc1ccccc1C(Cl)(c2ccccc2)c3ccccc3

InChI

1S/C19H14Cl2/c20-18-14-8-7-13-17(18)19(21,15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H

InChI key

JFLSOKIMYBSASW-UHFFFAOYSA-N

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Application

  • Acid labile resin used in Fmoc-based solid phase peptide synthesis.
  • Mild acidic cleavage conditions lead to the release of the peptide acid where fully protected peptides can be released if desired.
  • 2-Chlorotrityl chloride resins prevent racemization of the first amino acid and are thus very useful when racemic mixtures are forming (common with residues such as His or Cys).
  • This resin also prevents diketopiperazide formation, which can be an issue with proline C-terminal peptide sequences.

Use:
  • Attachment of the first amino acid residue is effected by stirring the resin, the protected amino acid, and excess diisopropylethylamine (DIEA) in dichloromethane.
  • Cleavage of the final protected peptide fragment is achieved under very mild conditions using either acetic acid/trifluoroethanol (TFE)/dichloromethane (1:1:8; v/v/v), hexafluoroisopropanol (HFIP)/dichloromethane (1:4; v/v) or simply 0.5% trifluoroacetic acid/dichloromethane (v/v).
  • Higher concentrations of TFA can be used if retention of peptide side chaing protecting groups is unimportant. Note that trityl chloride is moisture-sensitive, and, therefore, should be stored and handled appropriately.
  • If the resin becomes deactivated, treatment with acetyl chloride or SOCl2 in toluene before use is recommended to restore its activity.

Pictograms

CorrosionExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Met. Corr. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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