Amino acids attached to 2-chlorotrityl resins

Amino acid-2-chlorotrityl resins are used for the preparation of both protected peptide fragments and fully deprotected peptide acids. If the finished peptide resin is cleaved with AcOH/TFE/DCM (2:2:6), 0.5% TFA in DCM or 30% HFIP in DCM, it would give protected peptide acid fragment without any loss of side-chain protecting groups [1-7]. If the peptide resin is cleavage with 95% TFA and scavengers, it would yield fully deprotected peptide acid. Peptides containing C-terminal Cys, His and Pro residues are highly recommended to use the 2-chlorotrityl resins instead of the corresponding Wang resins. The reaction for loading the amino acid on 2-chlorotrityl resin does not cause any racemization, but it is well known that there is serious racemization problem to loading Cys and His on Wang resin even by using the most advanced technique. H-Pro-2-chlorotrityl resin is excellent support to prepare N-terminal Pro peptide as the bulk of the trityl handle prevents diketopiperazine formation. The substitution rate of amino acid on resin is determined by photometric measuring the Fmoc-chromophore liberated upon treatment with piperidine/DMF. The Fmoc group has been removed as the free amino-2-chlorotrityl resin has better stability.

[1] K. Barlos, et al, Tetrahedron Lett., 1989, 30, 3943.

[2] K. Barlos, et al, Tetrahedron Lett., 1989, 30, 3947.

[3] K. Barlos, et al, Angew. Chem., 1991, 103, 572.

[4] K. Barlos, et al, Int. J. Peptide Protein Res., 1991, 37, 513.

[5] K. Barlos, et al, Int. J. Peptide Protein Res., 1991, 38, 562.

[6] K. Barlos, et al, Int. J. Peptide Protein Res., 1991, 38, 555.

[7] K. Barlos, et al, Ann. Chem., 1993, 215.

11011

L-Alanine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11012

D-Alanine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$90

$380

$1,520

 

11021

(Ng -2,2,4,6,7-Pentamethyl-dihydrobenzo-

furan-5-sulfonyl)-L-arginine

2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$100

$415

$1,660

 

11022

(Ng -2,2,4,6,7-Pentamethyl-dihydrobenzo-

furan-5-sulfonyl)-D-arginine

2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$140

$580

$2,320

 

11031

(Nb -Trityl)-L-asparagine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11033

L-Asparagine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$240

$960

 

11034

D-Asparagine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$140

$560

$2,240

 

11041

(b -t-butyl ester)-L-aspartic acid 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11042

(b -t-Butyl ester)-D-aspartic acid

2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$140

$560

$2,240

 

11051

(S-Trityl)-L-cysteine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11052

(S-Trityl)-D-cysteine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$180

$700

$2,800

 

11053

(S-Acetamidomethyl)-L-cysteine

2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11061

(Ng -Trityl)-L-glutamine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11063

L-Glutamine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11064

D-Glutamine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$140

$560

 

11071

(g -t-Butyl ester)-L-glutamic acid 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11072

(g -t-Butyl ester)-D-glutamic acid 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

$140

$560

11081

Glycine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11091

( Nim-Trityl)-L-histidine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11092

( Nim-Trityl)-D-histidine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$170

$670

 

11101

L-Isoleucine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11111

L-Leucine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11112

D-Leucine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$90

$370

 

11121

(Ne -t-Butyloxycarbonyl)-L-lysine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11122

(Ne -t-Butyloxycarbonyl)-D-lysine2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

$140

$560

 

11131

L-Methionine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11132

D-Methionine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$90

$370

 

11141

L-Phenylalanine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11142

D-Phenylalanine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$90

$370

$1,480

 

11151

L-Proline 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11152

D-Proline 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$90

$370

 

11163

(O-t-Butyl ether)-L-serine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11164

(O-t-Butyl ether)-D-serine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$140

$560

 

11173

(O-t-Butyl ether)-L-threonine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11174

(O-t-butyl ether)-D-threonine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$140

$560

 

11181

L-Tryptophan 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11182

D-tryptophan 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$110

$460

 

11183

(Nin-t-butyloxycarbonyl)-L-tryptophan

2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene-

1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11193

(O-t-butyl ether)-L-tyrosine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$95

$380

$1,520

 

11194

(O-t-butyl ether)-D-tyrosine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

$140

$570

 

11201

L-Valine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$60

$250

$1,000

 

11202

D-Valine 2-chlorotrityl resin

Substitution: 0.3 - 0.8 mmole/g resin

Bead size 200- 400 mesh (polystyrene- 1% DVB)

1 g

5 g

25 g

$90

$380

$1,520