Fmoc-O-trityl-L-threonine
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Fmoc-O-trityl-L-threonine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003822
CAS number
133180-01-5
Molecular Formula
C38H33NO5
Molecular Weight
583.70
Fmoc-O-trityl-L-threonine
IUPAC Name
(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxybutanoic acid
Synonyms
Fmoc-L-Thr(Trt)-OH; Na-Fmoc-Thr(O-trityl)-OH; Fmoc-O-trityl-L-threonine; Fmoc-Thr(Trt)-OH
Appearance
White to off-white crystalline powder
Purity
≥ 99.7% (HPLC, Chiral purity)
Density
1.241±0.06 g/cm3
Melting Point
70-75 °C
Boiling Point
753.0±60.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H33NO5/c1-26(44-38(27-15-5-2-6-16-27,28-17-7-3-8-18-28)29-19-9-4-10-20-29)35(36(40)41)39-37(42)43-25-34-32-23-13-11-21-30(32)31-22-12-14-24-33(31)34/h2-24,26,34-35H,25H2,1H3,(H,39,42)(H,40,41)/t26-,35+/m1/s1
InChI Key
JARBLLDDSTVWSM-IJAHGLKVSA-N
Canonical SMILES
CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6
1.Chemical synthesis and receptor binding of catfish somatostatin: a disulfide-bridged beta-D-Galp-(1-->3)-alpha-D-GalpNAc O-glycopeptide.
Chen L1, Jensen KJ, Tejbrant J, Taylor JE, Morgan BA, Barany G. J Pept Res. 2000 Jan;55(1):81-91.
The glycopeptide hormone catfish somatostatin (somatostatin-22) has the amino acid sequence H-Asp-Asn-Thr-Val-Thr-Ser-Lys-Pro-Leu-Asn-Cys-Met-Asn-Tyr-Phe-Trp-Lys-Se r-Arg-Thr-Ala-Cys-OH; it includes a cyclic disulfide connecting the two Cys residues, and the major naturally occurring glycoform contains D-GalNAc and D-Gal O-glycosidically linked to Thr5. The linear sequence was assembled smoothly starting with an Fmoc-Cys(Trt)-PAC-PEG-PS support, using stepwise Fmoc solid-phase chemistry. In addition to the nonglycosylated peptide, two glycosylated forms of somatostatin-22 were accessed by incorporating as building blocks, respectively, Nalpha-Fmoc-Thr(Ac3-alpha-D-GalNAc)-OH and Nalpha-Fmoc-Thr(Ac4-beta-D-Gal-(1-->3)-Ac2-alpha-D-GalNAc)-O H. Acidolytic deprotection/cleavage of these peptidyl-resins with trifluoroacetic acid/scavenger cocktails gave the corresponding acetyl-protected glycopeptides with free sulfhydryl functions. Deacetylation, by methanolysis in the presence of catalytic sodium methoxide, was followed by mild oxidation at pH 7, mediated by Nalpha-dithiasuccinoyl (Dts)-glycine, to provide the desired monomeric cyclic disulfides.
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