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Structure

Fmoc-Tyr(tBu)-Thr(psiMe,Mepro)-OH

CAS
920519-31-9
Catalog Number
ACM920519319-1
Category
Amino Acids
Molecular Weight
600.7

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Specification

Description
This pseudoproline dipeptide is undoubtedly the most effective and simplest to use tool for overcoming aggregation and enhancing peptide quality in Fmoc SPPS for peptide containing the Tyr-Thr dipeptide motif. It consists of a dipeptide in which the threonine residue has been reversibly protected as a structure-breaking proline-like TFA-labile oxazolidine. The reason the pseudoproline residue is introduced as a dipeptide is because it avoids the need to acylate the hindered oxazolidine nitrogen. This has the added advantage of extending the peptide chain by two residues in one step. The threonine residue is regenerated during the normal TFA-mediated cleavage reaction.
Synonyms
Fmoc-Tyr(tBu)-Thr(psiMe,Mepro)-OH
InChI
1S/C35H40N2O7/c1-21-30(32(39)40)37(35(5,6)43-21)31(38)29(19-22-15-17-23(18-16-22)44-34(2,3)4)36-33(41)42-20-28-26-13-9-7-11-24(26)25-12-8-10-14-27(25)28/h7-18,21,28-30H,19-20H2,1-6H3,(H,36,41)(H,39,40)/t21-,29+,30+/m1/s1
InChI Key
JYSMURJYNLWZNY-RIGQTMPJSA-N
Application
Peptide synthesis.
Assay
≥97% (TLC)
≥97.0% (HPLC)
Form
powder
Functional Group
hydroxyl
Quality Level
200
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
2-8℃
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