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8.52184

Fmoc-Leu-Thr(psiMe,Mepro)-OH

≥97.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-Leu-Thr(psiMe,Mepro)-OH

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About This Item

Empirical Formula (Hill Notation):
C28H34N2O6
CAS Number:
955048-89-2
Molecular Weight:
494.58
MDL number:
MFCD03490500
UNSPSC Code:
12352209
NACRES:
NA.22
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Product Name

Fmoc-Leu-Thr(psiMe,Mepro)-OH, Novabiochem®

Quality Segment

200

product line

Novabiochem®

assay

≥97% (TLC), ≥97.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

hydroxyl

storage temp.

2-8°C

SMILES string

N4([C@@H]([C@H](OC4(C)C)C)C(=O)O)C(=O)[C@@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)CC(C)C

InChI

1S/C28H34N2O6/c1-16(2)14-23(25(31)30-24(26(32)33)17(3)36-28(30,4)5)29-27(34)35-15-22-20-12-8-6-10-18(20)19-11-7-9-13-21(19)22/h6-13,16-17,22-24H,14-15H2,1-5H3,(H,29,34)(H,32,33)/t17-,23+,24+/m1/s1

InChI key

OTDJFZHIGWFIEW-CQLNOVPUSA-N

General 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 Leu-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.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Overcoming Aggregation in Fmoc SPPS

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Optical rotation α 25/D (c=1 in CH₂Cl₂): -33.0 - -28.0 °
Purity (TLC(CMA2)): ≥ 97 %
Purity (TLC(157A)): ≥ 97 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Single impurities (HPLC, area%): ≤ 2.00 % (a/a)
Acetate (IC): ≤ 0.1 %
Ethyl acetate (HS-GC): ≤ 2.0 %

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

Other Notes

Replaces: 05-20-1009

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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