ChemInform Abstract: Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids.

ChemInform ◽  
2016 ◽  
Vol 47 (23) ◽  
Author(s):  
Amit Banerjee ◽  
Soundararasu Senthilkumar ◽  
Sundarababu Baskaran
Keyword(s):  
Amino Acids ◽  
Carboxylic Acid ◽  
Uronic Acids ◽  
Protecting Group ◽  
Sugar Amino Acids

scholarly journals Synthesis of chimera oligopeptide including furanoid β-sugar amino acid derivatives with free OHs: mild but successful removal of the 1,2-O-isopropylidene from the building block

Amino Acids ◽  
2021 ◽  
Vol 53 (2) ◽  
pp. 281-294
Author(s):  
Kim Hoang Yen Duong ◽  
Viktória Goldschmidt Gőz ◽  
István Pintér ◽  
András Perczel
Keyword(s):  
Amino Acids ◽  
Model Compound ◽  
Building Blocks ◽  
Membered Ring ◽  
Amino Acid Derivatives ◽  
Protecting Group ◽  
Sugar Amino Acids ◽  
Rp Hplc ◽  
Successful Removal ◽  
Chimeric Peptides

AbstractComplementary to hydrophobic five membered ring β-amino acids (e.g. ACPC), β-sugar amino acids (β-SAAs) have found increasing application as hydrophilic building blocks of foldamers and α/β chimeric peptides. Fmoc-protected β-SAAs [e.g. Fmoc-RibAFU(ip)-OH] are indeed useful Lego elements, ready to use for SPPS. The removal of 1,2-OH isopropylidene protecting group increasing the hydrophilicity of such SAA is presented here. We first used N3-RibAFU(ip)-OH model compound to optimize mild deprotection conditions. The formation of the 1,2-OH free product N3-RibAFU-OH and its methyl glycoside methyl ester, N3-RibAFU(Me)-OMe were monitored by RP-HPLC and found that either 50% TFA or 8 eqv. Amberlite IR-120 H+ resin in MeOH are optimal reagents for the effective deprotection. These conditions were then successfully applied for the synthesis of chimeric oligopeptide: -GG-X-GG- [X=RibAFU(ip)]. We found the established conditions to be effective and—at the same time—sufficiently mild to remove 1,2-O-isopropylidene protection and thus, it is proposed to be used in the synthesis of oligo- and polypeptides of complex sequence combination.

Synthesis and Antibacterial Potency of 4-Methyl-2,7-dioxo-1,2,3,4,7,10- hexahydropyrido[2,3-ƒ]quinoxaline-8-carboxylic acid, Selected [a]-Fused Heterocyles and Acyclic Precursors

2007 ◽  
Vol 62 (11) ◽  
pp. 1453-1458 ◽  
Author(s):  
Yusuf M. Al-Hiari ◽  
Ali M. Qaisia ◽  
Mohammad Y.Abu Shuheil ◽  
Mustafa M. El-Abadelah ◽  
Wolfgang Voelter
Keyword(s):  
Amino Acids ◽  
Carboxylic Acid ◽  
Antibacterial Activities ◽  
Sodium Dithionite ◽  
E Coli ◽  
Pipecolinic Acid

The reaction of 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) with each of sarcosine and (±)-pipecolinic acid afforded the corresponding N-(4- oxoquinolin-7-yl)-α-amino acids 8 and 9. Reductive lactamization of the latter with sodium dithionite gave hexahydropyrido[2,3- f ]quinoxaline (10) and octahydrodipyrido[1,2-a : 2,3- f ]quinoxaline (11) derivatives, respectively. Compounds 8 - 11 and their homologs 1 - 6, accessible from (S)-proline, (2S, 4R)-4-hydroxyproline and (S)-tetrahydroisoquinoline-3-carboxylic acid exhibit good to excellent antibacterial activities against E. coli and S. aureus.

The 4-(methylthio)phenyl ester for the synthesis of polypeptides of a known repeating sequence of amino acids. Synthesis of poly-(L-lysylglycyl)glycine 1-C14 ethyl ester hydrobromide

1970 ◽  
Vol 48 (16) ◽  
pp. 2509-2511 ◽  
Author(s):  
Brian J. Johnson ◽  
Donna S. Rea
Keyword(s):  
Amino Acids ◽  
Ethyl Ester ◽  
Title Compound ◽  
Ester Hydrochloride ◽  
Phenyl Ester ◽  
Protecting Group ◽  
High Dilution ◽  
Protective Groups ◽  
Protected Tetrapeptide

The synthesis of the tetrapeptide, N-t-butoxycarbonyl-ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylthio)phenyl ester is described. The utility of this protective ester is shown by its easy conversion to the protected tetrapeptide 4-(methylsulfonyl)phenyl activated ester without decomposition. Removal of the N-butoxycarbonyl protecting group afforded the polymerizing unit, ε-N-carbobenzoxy-L-lysylglycyl-ε-N-carbobenzoxy-L-lysylglycine 4-(methylsulfonyl)phenyl ester. Polymerization of this material on the partially blocked monomer glycine-1-C14 ethyl ester hydrochloride, at a relatively high dilution, gave poly-(ε-N-carbobenzoxyl-L-lysylglycyl)glycine-1-C14 ethyl ester. The carbobenzoxy protective groups were removed to give the title compound.

Spectroscopic studies of oligomers containing 2,5-transfuranoid sugar amino acids

Chirality ◽  
2008 ◽  
Vol 20 (9) ◽  
pp. 969-972 ◽  
Author(s):  
Alison A. Edwards ◽  
Bruce D. Alexander ◽  
George W. J. Fleet ◽  
George E. Tranter
Keyword(s):  
Amino Acids ◽  
Spectroscopic Studies ◽  
Sugar Amino Acids

Synthesis and structure determination of some sugar amino acids related to alanine and 6-deoxymannojirimycin

2001 ◽  
Vol 332 (4) ◽  
pp. 351-361 ◽  
Author(s):  
Miroslav Koóš ◽  
Bohumil Steiner ◽  
Júlia Mičová ◽  
Vratislav Langer ◽  
Marián Ďurı́k ◽  
...  
Keyword(s):  
Amino Acids ◽  
Structure Determination ◽  
Sugar Amino Acids

Sugar Amino Acids and Their Uses in Designing Bioactive Molecules

2002 ◽  
Vol 9 (4) ◽  
pp. 421-435 ◽  
Author(s):  
Tushar Chakraborty ◽  
Subhash Ghosh ◽  
Sarva Jayaprakash
Keyword(s):  
Amino Acids ◽  
Bioactive Molecules ◽  
Sugar Amino Acids

Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

2016 ◽  
Vol 14 (44) ◽  
pp. 10473-10480 ◽  
Author(s):  
Sylvain Daunay ◽  
Remi Lebel ◽  
Laurence Farescour ◽  
Jean-Claude Yadan ◽  
Irene Erdelmeier
Keyword(s):  
Amino Acids ◽  
Protecting Group ◽  
One Pot ◽  
Step Procedure ◽  
Sulfur Containing

Natural and novel sulfur-containing amino acids are preparedviaa new regioselective one-pot two-step procedure.

Enzymatic resolution of (±)-5-phenyl-4,5-dihydroisoxazole-3-carboxylic acid ethyl ester and its transformations into polyfunctionalised amino acids and dipeptides

2009 ◽  
Vol 20 (16) ◽  
pp. 1940-1947 ◽  
Author(s):  
Giuseppe Cremonesi ◽  
Piero Dalla Croce ◽  
Alessandra Forni ◽  
Maddalena Gallanti ◽  
Raffaella Gandolfi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Acid Ethyl Ester ◽  
Enzymatic Resolution
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