Fmoc-N-methyl-L-norleucine
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Fmoc-N-methyl-L-norleucine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007464
CAS number
112883-42-8
Molecular Formula
C22H25NO4
Molecular Weight
367.44
Fmoc-N-methyl-L-norleucine
IUPAC Name
(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]hexanoic acid
Synonyms
Fmoc-N-Me-L-Nle-OH; Fmoc-N-methyl-L-2-aminohexanoic acid; Fmoc N Me L Nle OH
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.196±0.06 g/cm3
Melting Point
112-125 °C
Boiling Point
542.6±29.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H25NO4/c1-3-4-13-20(21(24)25)23(2)22(26)27-14-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,19-20H,3-4,13-14H2,1-2H3,(H,24,25)/t20-/m0/s1
InChI Key
RZZXDYZWHUAOEK-FQEVSTJZSA-N
Canonical SMILES
CCCCC(C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1.Efficient Fmoc/solid-phase peptide synthesis of O-phosphotyrosyl-containing peptides and their use as phosphatase substrates.
Perich JW1, Ruzzene M, Pinna LA, Reynolds EC. Int J Pept Protein Res. 1994 Jan;43(1):39-46.
A general synthetic method for the efficient preparation of Tyr(P)-containing peptides is described by the use of Fmoc-Tyr(PO3tBu2)-OH in Fmoc/solid-phase synthesis followed by simultaneous cleavage of the peptide from the resin and peptide deprotection by acidolytic treatment. The applicability of this approach is demonstrated by the synthesis of H-Ser-Ser-Ser-Tyr(P)-Tyr(P)-OH.TFA and the synthesis of the phosphorylated forms of the two physiological peptides, angiotensin II and neurotensin 8-13. In addition, the three phosphorylated peptides were used as substrates in the study of the local specificity determinants of T-cell protein tyrosine phosphatase. In a competition assay using 32P-radiolabeled [Tyr(P)]4-angiotensin II, both unlabeled synthetic [Tyr(P)]4-angiotensin II and Ser-Ser-Ser-Tyr(P)-Tyr(P) reduced the release of 32P and indicated that they efficiently competed as substrates for the phosphatase. Conversely, [Tyr(P)]4-neurotensin 8-13 was ineffective as a competitive substrate and indicated that this particular Tyr(P)-containing peptide sequence was not recognized by the enzyme.
2.Transglycosylation of intact sialo complex-type oligosaccharides to the N-acetylglucosamine moieties of glycopeptides by Mucor hiemalis endo-beta-N-acetylglucosaminidase.
Haneda K1, Inazu T, Yamamoto K, Kumagai H, Nakahara Y, Kobata A. Carbohydr Res. 1996 Oct 4;292:61-70.
The endo-beta-N-acetylglucosaminidase (endo-beta-GlcNAc-ase) of Mucor hiemalis, endo-M, was found to transfer the sialo complex-type oligosaccharides from transferrin glycopeptide to the N-acetylglucosamine (GlcNAc) moieties of peptidyl-GlcNAc. Disialo complex-type oligosaccharide of transferrin glycopeptide was transferred to 9-fluorenylmethyloxycarbonyl (Fmoc)-asparaginyl-N-acetylglucosaminide (Fmoc-Asn-GlcNAc) by endo-M in a high yield. The structure of the reaction product was confirmed to be Fmoc-Asn-(GlcNAc)2-Man-(Man-GlcNac-Gal-NeuAc)2 by mass spectrometry. Endo-M also transferred disialo complex-type oligosaccharide to the GlcNAc residue of chemically synthesized H-Ile-Asn(GlcNAc)-Ala-Thr-Leu-OH. Asn-linked asialo complex-type oligosaccharide and Asn-linked high-mannose type oligosaccharide were also effective as oligosaccharide donors. Transfer of disialo complex-type oligosaccharide to the GlcNAc-peptide was the most effective among the three types of oligosaccharides, although the disialo complex-type oligosaccharide attached to the peptide was the poorest substrate for the hydrolytic activity of endo-M.
3.Synthesis of N-(Hydroxy)amide- and N-(Hydroxy)thioamide-containing peptides.
Wang L1, Phanstiel O 4th. J Org Chem. 2000 Mar 10;65(5):1442-7.
Methods developed with N-(benzoyloxy)amines and hydroxamic acids were used in the synthesis of N-(hydroxy)amide-containing pseudopeptides. Acylation of N-(benzoyloxy)phenethylamine with the acid chloride of N(alpha)-Fmoc-L-leucine provided a N(alpha)-Fmoc-N-(benzoyloxy)-L-leucinamide in 90% yield. Deprotection of the benzoyl group (using 10 vol % NH(4)OH/MeOH) provided the N(alpha)-Fmoc-N-(hydroxy)-L-leucinamide in 87% yield. In general, the appended Fmoc group allowed for further elaboration of the N-hydroxy-N-(alkyl)amides using classic peptide-coupling methods. A practical synthetic strategy was developed, and racemization issues were addressed using diastereomeric Val-Leu derivatives. In addition, N-(hydroxy)thioamides were generated from the corresponding N-(benzoyloxy)thioamides. N-(Benzoyloxy)thioamides were obtained in moderate yields (53-76%) from the reaction of the corresponding N-(benzoyloxy)amides with Lawesson's reagent (i.
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