8.52075

Fmoc-Orn(Mtt)-OH

Novabiochem^®

• Synonym(s): Fmoc-Orn(Mtt)-OH, N-α-Fmoc-N-δ-4-methyltrityl-L-ornithine
• Empirical Formula (Hill Notation): C₄₀H₃₈N₂O₄
• CAS Number: 343770-23-0
• Molecular Weight: 610.74
• MDL number: MFCD00797872
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Segment: 200
• product line: Novabiochem^®
• assay: ≥90.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: amine
• storage temp.: 15-25°C
• SMILES string: N([C@@H](CCCNC(c6ccc(cc6)C)(c5ccccc5)c4ccccc4)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C40H38N2O4/c1-28-22-24-31(25-23-28)40(29-13-4-2-5-14-29,30-15-6-3-7-16-30)41-26-12-21-37(38(43)44)42-39(45)46-27-36-34-19-10-8-17-32(34)33-18-9-11-20-35(33)36/h2-11,13-20,22-25,36-37,41H,12,21,26-27H2,1H3,(H,42,45)(H,43,44)/t37-/m0/s1
• InChI key: RRYSGISHZIBOJC-QNGWXLTQSA-N

Description

General description

The side-chain Mtt group can be selectively removed with 1% TFA in DCM ^[1,2,3] or DCM/HFIP/TFE/TES (6.5:2:1:0.5) ^[4], making this an excellent derivative for the synthesis by Fmoc SPPS of branched peptides, peptides modified at the ornithine side-chain ^[4,5], for the construction of templates and multifunctionalized resins for combinatorial synthesis ^[6].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] K. Barlos, et al., C. H. Schneider & A. N. Eberle (Eds), ESCOM, Leiden, 1993, pp. 283.
^[2] A. Aletras, et al. (1995) Int. J. Peptide Protein Res., 45, 488.
^[3] L. Bourel, et al. (2000) J. Peptide Sci., 6, 264.
^[4] K. Barlos, personal communication.
^[5] P. Hoogerhout, et al. (1999) J. Peptide Res., 54, 436.
^[6] C. Park & K. Burgess (2001) J. Comb. Chem., 3, 257.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(CMA2)): ≥ 98 %
Purity (TLC(011C)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 1.0 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1168

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable