Peptides & Peptide Synthesis Products
Fmoc-D-His(Trt)-OH
Catalog No: 42008
Nα-Fmoc-N(im)-trityl-D-histidine, CAS: 135610-90-1, MW: 619.71, Formula: C40H33N3O4
Nα-Fmoc-N(im)-trityl-D-histidine, CAS: 135610-90-1, MW: 619.71, Formula: C40H33N3O4
$12.00
SKU
42008
Fmoc-D-His(Trt)-OH
Nα-Fmoc-Nim-trityl-D-histidine
The D-enantiomer of Fmoc-His(Trt)-OH, for introducing D-histidine in Fmoc SPPS. The trityl group on the imidazole is removed in the final TFA cleavage, with scavengers such as TIS.
Histidine racemizes particularly easily during activation, because the imidazole nitrogen nearest the backbone can remove the α-proton — here that would convert the D-residue back to L. Use a coupling protocol chosen for low racemization — carbodiimide activation with an additive rather than a strong base, short pre-activation, no heating.
Applications
- D-histidine substitutions tested for added protease stability
- Mirror-image (all-D) peptides and proteins
- D-amino acid scans and retro-inverso designs
Storage
Store refrigerated (2–8 °C) in a tightly closed container, and let it reach room temperature before opening.
References
- Sieber P et al. Protection of histidine in peptide synthesis: A Reassessment of the trityl group. Tetrahedron Letters 1987, 28, 6031–6034. doi:10.1016/S0040-4039(00)96856-4
For research use only. Not for human or veterinary use.
| Catalog Number | 42008 |
|---|---|
| CAS | 135610-90-1 |
| M.W. | 619.71 |
| Formula | C40H33N3O4 |
| IUPAC Name | (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-tritylimidazol-4-yl)propanoic acid |
| Synonym | Nα-Fmoc-N(im)-trityl-D-histidine |
| Also Known As |
|
| InChIKey | XXMYDXUIZKNHDT-DIPNUNPCSA-N |
| InChI | InChI=1S/C40H33N3O4/c44-38(45)37(42-39(46)47-26-36-34-22-12-10-20-32(34)33-21-11-13-23-35(33)36)24-31-25-43(27-41-31)40(28-14-4-1-5-15-28,29-16-6-2-7-17-29)30-18-8-3-9-19-30/h1-23,25,27,36-37H,24,26H2,(H,42,46)(H,44,45)/t37-/m1/s1 |
| SMILES | C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=C(N=C4)C[C@H](C(=O)O)NC(=O)OCC5C6=CC=CC=C6C7=CC=CC=C57 |
The current Safety Data Sheet for Fmoc-D-His(Trt)-OH (Catalog No: 42008).
The Certificate of Analysis for each lot of Fmoc-D-His(Trt)-OH (Catalog No: 42008). Enter the lot number printed on the product label.
Write Your Own Review