Fmoc-D-beta-homoSer(Me)-OH
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Fmoc-D-beta-homoSer(Me)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008427
CAS number
2171204-00-3
Molecular Formula
C20H21NO5
Molecular Weight
355.4
IUPAC Name
(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxybutanoic acid
Synonyms
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxybutanoic acid
Density
1.3±0.1 g/cm3
Boiling Point
589.0±50.0 °C at 760 mmHg
InChI
InChI=1S/C20H21NO5/c1-25-11-13(10-19(22)23)21-20(24)26-12-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,13,18H,10-12H2,1H3,(H,21,24)(H,22,23)/t13-/m0/s1
InChI Key
SPAKJEFERJUBAX-ZDUSSCGKSA-N
Canonical SMILES
COCC(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. Low-Dimensional Architectures in Isomeric cis-PtCl2{Ph2PCH2N(Ar)CH2PPh2} Complexes Using Regioselective-N(Aryl)-Group Manipulation
Peter De'Ath, Mark R J Elsegood, Noelia M Sanchez-Ballester, Martin B Smith Molecules. 2021 Nov 11;26(22):6809. doi: 10.3390/molecules26226809.
The solid-state behaviour of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to PtII, have been extensively studied using single crystal X-ray crystallography. In the first library, isomeric diphosphines of the type Ph2PCH2N(Ar)CH2PPh2 [1a-e; Ar = C6H3(Me)(OH)] and, in the second library, amide-functionalised, isomeric ligands Ph2PCH2N{CH2C(O)NH(Ar)}CH2PPh2 [2a-e; Ar = C6H3(Me)(OH)], were synthesised by reaction of Ph2PCH2OH and the appropriate amine in CH3OH, and isolated as colourless solids or oils in good yield. The non-methyl, substituted diphosphines Ph2PCH2N{CH2C(O)NH(Ar)}CH2PPh2 [2f, Ar = 3-C6H4(OH); 2g, Ar = 4-C6H4(OH)] and Ph2PCH2N(Ar)CH2PPh2 [3, Ar = 3-C6H4(OH)] were also prepared for comparative purposes. Reactions of 1a-e, 2a-g, or 3 with PtCl2(η4-cod) afforded the corresponding square-planar complexes 4a-e, 5a-g, and 6 in good to high isolated yields. All new compounds were characterised using a range of spectroscopic (1H, 31P{1H}, FT-IR) and analytical techniques. Single crystal X-ray structures have been determined for 1a, 1b∙CH3OH, 2f∙CH3OH, 2g, 3, 4b∙(CH3)2SO, 4c∙CHCl3, 4d∙½Et2O, 4e∙½CHCl3∙½CH3OH, 5a∙½Et2O, 5b, 5c∙¼H2O, 5d∙Et2O, and 6∙(CH3)2SO. The free phenolic group in 1b∙CH3OH, 2f∙CH3OH,2g, 4b∙(CH3)2SO, 5a∙½Et2O, 5c∙¼H2O, and 6∙(CH3)2SO exhibits various intra- or intermolecular O-H∙∙∙X (X = O, N, P, Cl) hydrogen contacts leading to different packing arrangements.
2. α/β-Chimera peptide synthesis with cyclic β-sugar amino acids: the efficient coupling protocol
Adrienn Nagy, Viktória Goldschmidt Gőz, István Pintér, Viktor Farkas, András Perczel Amino Acids. 2019 Apr;51(4):669-678. doi: 10.1007/s00726-019-02702-9. Epub 2019 Feb 13.
The synthesis of α/β-chimeras comprises peptide bond formation from α- to β-, from β- to β-, and from β- to α-amino acid residues. The fine-tuned solid phase synthesis of -GXXG- chimera peptides containing the simplest achiral α-amino acid glycine and two cyclic SAAs of different ring size [X denoting cyclic β-Sugar Amino Acids (β-SAA)] is reported, variants containing Fmoc-RibAFU(ip)-OH a furanoid-, and Fmoc-GlcAPU(Me)-OH a pyranoid-type structural "Lego-element". Systematic search for the best coupling strategy with both H-β-SAA-OHs is described, including the comparison of the different coupling reagents and conditions. Selecting the optimal reagent (from commonly used PyBOP, HATU and HOBt) was assisted by time-resolved 1H-NMR: formation and stability of the Fmoc protected active esters were compared. We found that PyBOP is the best choice for successfully coupling both H-β-SAA-OH prototypes. The present comparative results open a reasonable route for building efficiently various -β-SAA- containing homo- and heterooligomers.
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