Fmoc-3,4-dichloro-L-phenylalanine
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Fmoc-3,4-dichloro-L-phenylalanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007333
CAS number
177966-59-5
Molecular Formula
C24H19Cl2NO4
Molecular Weight
456.32
Fmoc-3,4-dichloro-L-phenylalanine
IUPAC Name
(2S)-3-(3,4-dichlorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-L-Phe(3,4-DiCl)-OH; Fmoc-L-Phe(3,4-Cl2)-OH; (S)-Fmoc-2-amino-3-(3,4-dichlorophenyl)propionic acid
Related CAS
177966-58-4 (D-isomer)
Appearance
White to off-white solid
Purity
≥ 98% (HPLC)
Density
1.394 g/cm3
Melting Point
112-120 °C
Boiling Point
661.7°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H19Cl2NO4/c25-20-10-9-14(11-21(20)26)12-22(23(28)29)27-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-11,19,22H,12-13H2,(H,27,30)(H,28,29)/t22-/m0/s1
InChI Key
QNVHCYWPXIGFGN-QFIPXVFZSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)Cl)Cl)C(=O)O
1.Carbohydrate-based synthetic approach to control toxicity profiles of folate-drug conjugates.
Vlahov IR1, Santhapuram HK, You F, Wang Y, Kleindl PJ, Hahn SJ, Vaughn JF, Reno DS, Leamon CP. J Org Chem. 2010 Jun 4;75(11):3685-91. doi: 10.1021/jo100448q.
To better regulate the biodistribution of the vinblastine-folate conjugate, EC145, a new folate-spacer that incorporates 1-amino-1-deoxy-D-glucitol-gamma-glutamate subunits into a peptidic backbone, was synthesized. Synthesis of Fmoc-3,4;5,6-di-O-isopropylidene-1-amino-1-deoxy-D-glucitol-gamma-glutamate 20, suitable for Fmoc-strategy solid-phase peptide synthesis (SPPS), was achieved in four steps from delta-gluconolactone. Addition of alternating glutamic acid and 20 moieties onto a cysteine-loaded resin, followed by the addition of folate, deprotection, and cleavage, resulted in the isolation of the new folate-spacer: Pte-gammaGlu-(Glu(1-amino-1-deoxy-D-glucitol)-Glu)(2)-Glu(1-amino-1-deoxy-D-glucitol)-Cys-OH (21). The addition of 21 to an appropriately modified desacetylvinblastine hydrazide (DAVLBH) resulted in a conjugate (25) with an improved therapeutic index. Treatment of 25 with DTT in neutral buffer at room temperature demonstrated that free DAVLBH would be released under the reductive environment of the internalized endosome.
2.Making Ends Meet: Microwave-Accelerated Synthesis of Cyclic and Disulfide Rich Proteins Via In Situ Thioesterification and Native Chemical Ligation.
Gunasekera S1, Aboye TL, Madian WA, El-Seedi HR, Göransson U. Int J Pept Res Ther. 2013 Mar;19(1):43-54. Epub 2012 Oct 14.
The development of synthetic methodologies for cyclic peptides is driven by the discovery of cyclic peptide drug scaffolds such as the plant-derived cyclotides, sunflower trypsin inhibitor 1 (SFTI-1) and the development of cyclized conotoxins. Currently, the native chemical ligation reaction between an N-terminal cysteine and C-terminal thioester group remains the most robust method to obtain a head-to-tail cyclized peptide. Peptidyl thioesters are effectively generated by Boc SPPS. However, their generation is challenging using Fmoc SPPS because thioester linkers are not stable to repeated piperidine exposure during deprotection. Herein we describe a Fmoc-based protocol for synthesizing cyclic peptides adapted for microwave assisted solid phase peptide synthesis. The protocol relies on the linker Di-Fmoc-3,4-diaminobenzoic acid, and we demonstrate the use of Gly, Ser, Arg and Ile as C-terminal amino acids (using HBTU and HATU as coupling reagents).
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