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N-α-(9-Fluorenylmethoxycarbonyl)-α-methyl-L-α-(7-octenyl)glycine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-methyl-9-decenoic acid, also called (S)-N-Fmoc-2-(7'-octenyl) alaninean alpha-AlkenylAla, which can connected to a natural amino acid at its N-terminal position for developing a range di-peptides.

Category

Amino Acids for Stapled Peptide

Catalog number

BAT-005495

CAS number

288617-75-4

Molecular Formula

C26H31NO4

Molecular Weight

421.54

N-α-(9-Fluorenylmethoxycarbonyl)-α-methyl-L-α-(7-octenyl)glycine

Specification
Reference Reading

IUPAC Name

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyldec-9-enoic acid

Synonyms

Fmoc-(Me)Gly(Octenyl)-OH; N-α-(9-Fluorenylmethoxycarbonyl)-α-(7-octenyl)-D-alanine; (S)-N-Fmoc-2-(7'-octenyl) alanine; Fmoc-(S)-2-(7-octenyl)Ala-OH; Fmoc-(S)-2-amino-2-methyl-dec-6-enoic acid; Fmoc-α-Me-Gly(octenyl)-OH

Appearance

Off-white semisolid

Purity

≥ 98% (Chiral HPLC, HPLC)

Density

1.140 g/cm3

Boiling Point

588.3±45.0 °C

Storage

Store at RT

Application

Pharmaceutical intermediates: used in solid phase peptide synthesis

InChI

1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m0/s1

InChI Key

MADFVGMQNXRFAF-SANMLTNESA-N

Canonical SMILES

CC(CCCCCCC=C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

1.Preparation of orthogonally protected (2S, 3R)-2-amino-3-methyl-4-phosphonobutyric acid (Pmab) as a phosphatase-stable phosphothreonine mimetic and its use in the synthesis of Polo-box domain-binding peptides.

Liu F1, Park JE2, Lee KS2, Burke TR Jr1. Tetrahedron. 2009 Nov 21;65(47):9673-9679.

Reported herein is the first stereoselective synthesis of (2S,3R)-4-[bis-(tert-butyloxy)phosphinyl]-2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-3-methylbutanoic acid [(N-Fmoc, O,O-(bis-(tert-butyl))-Pmab, 4] as a hydrolytically-stable phosphothreonine mimetic bearing orthogonal protection compatible with standard solid-phase protocols. The synthetic approach used employs Evans' oxazolidinone for chiral induction. Also presented is the application of 4 in the solid-phase synthesis of polo-like kinase 1 (Plk1) polo box domain (PBD)-binding peptides. These Pmab-containing peptides retain PBD binding efficacy similar to a parent pThr containing peptide. Reagent 4 should be a highly useful reagent for the preparation of signal transduction-directed peptides.