Fmoc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid
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Fmoc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid

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Category
Fmoc-Amino Acids
Catalog number
BAT-007269
CAS number
178432-50-3
Molecular Formula
C25H21NO5
Molecular Weight
415.43
Fmoc-(3R)-1,2,3,4-tetrahydroisoquinoline-7-hydroxy-3-carboxylic acid
IUPAC Name
(3R)-2-(9H-fluoren-9-ylmethoxycarbonyl)-7-hydroxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
Synonyms
Fmoc-D-Tic(OH)-OH
Purity
≥ 99% (HPLC)
Melting Point
192-198°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H21NO5/c27-17-10-9-15-12-23(24(28)29)26(13-16(15)11-17)25(30)31-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-11,22-23,27H,12-14H2,(H,28,29)/t23-/m1/s1
InChI Key
ZBLZSUJEVZOPJV-HSZRJFAPSA-N
Canonical SMILES
C1C(N(CC2=C1C=CC(=C2)O)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C(=O)O
1. 3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA
Nisanath Reenabthue, Chalothorn Boonlua, Chotima Vilaivan, Tirayut Vilaivan, Chaturong Suparpprom Bioorg Med Chem Lett. 2011 Nov 1;21(21):6465-9. doi: 10.1016/j.bmcl.2011.08.079. Epub 2011 Aug 23.
Conformationally restricted pyrrolidinyl PNAs with an α/β-dipeptide backbone consisting of a nucleobase-modified proline and a cyclic five-membered amino acid spacer such as (1S,2S)-2-aminocyclopentanecarboxylic acid (ACPC) (acpcPNA) can form very stable hybrids with DNA with high Watson-Crick base pairing specificity. This work aims to explore the effect of incorporating 3-aminopyrrolidine-4-carboxylic acid (APC), which is isosteric to the ACPC spacer, into the acpcPNA. It is expected that the modification should not negatively affect the DNA binding properties, and that the additional nitrogen atom in the APC should provide a handle for internal modification. Orthogonally-protected (N(3)-Fmoc/N(1)-Boc and N(3)-Fmoc/N(1)-Tfa) APC monomers have been successfully synthesized and incorporated into the acpcPNA by Fmoc-solid-phase peptide synthesis. T(m), UV and CD spectroscopy confirmed that the (3R,4S)-APC could substitute the (1S,2S)-ACPC spacer in the acpcPNA with only slightly decreasing the stability of the hybrids formed between the modified acpc/apcPNA and DNA. In contrast, the (3S,4R) enantiomer of APC caused substantial destabilization of the hybrids. Furthermore, a successful on-solid-support internal labeling of the acpc/apcPNA via amide bond formation between pyrene-1-carboxylic acid or 4-(pyrene-1-yl) butyric acid and the pyrrolidine nitrogen atom of the APC spacer has been demonstrated. Fluorescence properties of the pyrene-labeled acpc/apcPNAs are sensitive to their hybridization states and can readily distinguish between complementary and single-mismatched DNA targets.
2. Highly efficient and enantioselective syntheses of (2S,3R)-3-alkyl- and alkenylglutamates from Fmoc-protected Garner's aldehyde
Ryan Moreira, Scott D Taylor Amino Acids. 2020 Jul;52(6-7):987-998. doi: 10.1007/s00726-020-02868-7. Epub 2020 Jul 3.
A 6-step enantioselective synthesis of (2S,3R)-3-alkyl/alkenylglutamates, including the biologically significant amino acid, (2S,3R)-3-methylglutamate, protected for Fmoc SPPS, is reported. Overall yields range from 52-65%. Key to the success of these syntheses was the development of a high-yielding 2-step synthesis of Fmoc Garner's aldehyde followed by a Horner-Wadsworth-Emmons reaction to give the corresponding Fmoc Garner's enoate in a 94% yield. The diastereoselective 1,4-addition of lithium dialkylcuprates to the Fmoc Garner's enoate was explored. Significant decomposition occurred when using lithium diethylcuprate and conditions previously reported for the 1,4-addition of lithium dialkylcuprates to Boc or Cbz-protected Garner's enoate. An optimization study of this reaction resulted in a robust set of conditions that addressed the shortcomings of previously reported conditions. Under these conditions, highly diastereoselective (> 20:1 in most cases) 1,4-addition reactions of lithium dialkyl/dialkenylcuprates to the Fmoc Garner's enoate were achieved in 76-99% yield. The resulting 1,4-addition products were easily converted into the Fmoc-(2S,3R)-3-alkyl/alkenylglutamates in two steps.
3. Solid-Phase Synthesis of Octapeptin Lipopeptides
Karl A Hansford, Zyta M Ziora, Matthew A Cooper, Mark A T Blaskovich Methods Mol Biol. 2020;2103:199-213. doi: 10.1007/978-1-0716-0227-0_13.
Octapeptins are naturally derived cyclic lipopeptide antibiotics with activity against a range of Gram-negative pathogens, including highly resistant strains. Octapeptin C4, an exemplar of the class, was synthesized using a combination of Fmoc solid-phase peptide synthesis (SPPS) and solution-phase cyclization. Utilizing H-L-Leu-2-chlorotrityl resin, peptide couplings were performed using HCTU and collidine in DMF. The linear sequence was terminated by N-acylation with 3-(R)-hydroxydecanoic acid. The residue Dab-2 was orthogonally protected with 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)isovaleryl group (ivDde) to enable selective side-chain deprotection prior to resin cleavage. Resin cleavage was accomplished with hexafluoroisopropanol in DCM, followed by cyclization with diphenylphosphoryl azide (DPPA) and solid sodium bicarbonate in DMF.
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