Fmoc-O-tert-butyl-L-threonine 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine ester
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Fmoc-O-tert-butyl-L-threonine 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003816
CAS number
119767-84-9
Molecular Formula
C30H30N4O6
Molecular Weight
542.60
Fmoc-O-tert-butyl-L-threonine 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine ester
IUPAC Name
(4-oxo-1,2,3-benzotriazin-3-yl) (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoate
Synonyms
Fmoc-L-Thr(tBu)-ODhbt; FMOC-O-T-BUTYL-L-THREONINE 3,4-DIHYDRO-3-HYDROXY-4-OXO-1,2,3-BENZOTRIAZINE ESTER; N-Fmoc-O-t-butyl-L-threonine 3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine Ester
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.32 g/cm3
Melting Point
65-73 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C30H30N4O6/c1-18(39-30(2,3)4)26(28(36)40-34-27(35)23-15-9-10-16-25(23)32-33-34)31-29(37)38-17-24-21-13-7-5-11-19(21)20-12-6-8-14-22(20)24/h5-16,18,24,26H,17H2,1-4H3,(H,31,37)/t18?,26-/m0/s1
InChI Key
SBBDXSZBUHGNMB-IHZSNKTASA-N
Canonical SMILES
CC(C(C(=O)ON1C(=O)C2=CC=CC=C2N=N1)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)OC(C)(C)C
1. Powerful solvent systems useful for synthesis of sparingly-soluble peptides in solution
H Kuroda, Y N Chen, T Kimura, S Sakakibara Int J Pept Protein Res. 1992 Sep-Oct;40(3-4):294-9. doi: 10.1111/j.1399-3011.1992.tb00304.x.
Our maximum protection strategy for the synthesis of human parathyroid hormone(1-84) indicates that fully protected peptide segments in the form of Boc-peptide phenacyl (Pac) ester are relatively soluble in ordinary organic solvents such as DMF, NMP or DMSO, which are suitable for coupling segments. However, about 1% of such segments synthesized were found to be insoluble even in the most polar solvent, DMSO. Thus, a more powerful solvent which can be used for their peptide synthesis was pursued. Among the solvent systems tested, a mixture of trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and trichloromethane (TCM) or dichloromethane (DCM) was found to be most powerful for dissolving such sparingly-soluble protected peptides. These solvent systems were confirmed to be useful for the removal reaction of the carboxy-terminal Pac esters from the sparingly-soluble segments. They were then tested for the coupling reactions of fully protected Boc-peptides with other sparingly-soluble peptide esters. The TFE/TCM or TFE/DCM system was extremely useful for coupling segments without danger of racemization and of trifluoroester formation, if WSCI was used as the coupling reagent in the presence of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (HOOBt).
2. Effects of amounts of additives on peptide coupling mediated by a water-soluble carbodiimide in alcohols
S Nozaki J Pept Res. 1999 Aug;54(2):162-7. doi: 10.1034/j.1399-3011.1999.00101.x.
The optimal amounts of 1-hydroxybenzotriazole (HOBt), 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (HOOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) for enhancement of peptide coupling mediated by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride in alcoholic solvents were found to be less than equimolar against the carboxyl component or the carbodiimide. In comparison with the use of equimolar additives, the use of less equimolar ones was more effective in suppressing the competitive ester formation and in increasing the yield of desired peptides. EDC hydrochloride/around 0.1 equimolar HOAt or HOOBt were efficient reagents for peptide synthesis in the media.
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