Chemoenzymatic Synthesis and Synthetic Application of Enantiopure Aminocyclopentenols:  Total Synthesis of Carbocyclic (+)-Uracil Polyoxin C and Its α-Epimer

2004 ◽  
Vol 69 (13) ◽  
pp. 4538-4540 ◽  
Author(s):  
Fangzheng Li ◽  
John B. Brogan ◽  
Jennifer L. Gage ◽  
Deyi Zhang ◽  
Marvin J. Miller
Keyword(s):  
Total Synthesis ◽  
Chemoenzymatic Synthesis ◽  
Synthetic Application

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

scholarly journals Concise total synthesis of two marine natural nucleosides: trachycladines A and B

2014 ◽  
Vol 10 ◽  
pp. 1681-1685 ◽  
Author(s):  
Haixin Ding ◽  
Wei Li ◽  
Zhizhong Ruan ◽  
Ruchun Yang ◽  
Zhijie Mao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Starting Material ◽  
Chemoenzymatic Synthesis ◽  
Critical Step ◽  
Adenylate Deaminase

We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl4assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Chemoenzymatic Synthesis and Function of Chitin Derivatives

2020 ◽  
Vol 26 (29) ◽  
pp. 3522-3529 ◽  
Author(s):  
Makoto Ogata
Keyword(s):  
Total Synthesis ◽  
Raw Materials ◽  
Functional Materials ◽  
Chemoenzymatic Synthesis ◽  
Esterification Reaction ◽  
Marine Life ◽  
Egg White Lysozyme ◽  
Hen Egg White ◽  
And Function ◽  
Effective Use

Chitin, abundant biomass found in crab shells and other marine life, has wide applications in the production of food, pharmaceuticals, and cosmetics. Our recent studies have focused on the development of new functional materials by derivatizing chitin oligosaccharides and monosaccharides. For example, we have prepared various derivatives by chemoenzymatic synthesis using N-acetylglucosamine (GlcNAc) or chitin oligosaccharide prepared from chitin as starting materials. First, we have achieved the total synthesis of two secondary metabolites (furanodictine A and B) with neuronal differentiation-inducing activity on PC12 cells by using a simple heatinduced structural transformation of GlcNAc and esterification reaction. Second, we synthesized both a novel inhibitor that has facilitated a re-examination of the reaction mechanism of hen egg-white lysozyme, and a new substrate for assaying lysozyme activity by using chitin oligosaccharides as raw materials. Thus, the development of new materials by simple derivatization of chitin mono- or oligo-saccharides is paving the way for effective use of chitin.

scholarly journals A TOTAL SYNTHESIS OF (±)-WIDDROL. SYNTHETIC APPLICATION OF THE FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLO[3.2.2]NON-6-EN-2-ONES WITH ALKYL GROUPS

1986 ◽  
Vol 15 (4) ◽  
pp. 609-612 ◽  
Author(s):  
Tadao Uyehara ◽  
Jun-ichi Yamada ◽  
Toshiaki Furuta ◽  
Tadahiro Kato
Keyword(s):  
Total Synthesis ◽  
Alkyl Groups ◽  
Synthetic Application

A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

2010 ◽  
Vol 63 (10) ◽  
pp. 1437 ◽  
Author(s):  
Martin G. Banwell ◽  
Xinghua Ma ◽  
Ochitha P. Karunaratne ◽  
Anthony C. Willis
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Claisen Rearrangement ◽  
Starting Material ◽  
Chemoenzymatic Synthesis ◽  
Quaternary Carbon ◽  
Enantiomerically Pure ◽  
Rearrangement Reaction

A total synthesis of (+)-galanthamine [(+)-1] has been achieved using the readily available and enantiomerically pure metabolite 2 as starting material. The quaternary carbon centre (C8a) associated with target 1 was constructed using the Eschenmoser–Claisen rearrangement reaction.

Endohexosaminidase-catalyzed synthesis of glycopeptides and proteins

2013 ◽  
Vol 85 (9) ◽  
pp. 1847-1863 ◽  
Author(s):  
Antony J. Fairbanks
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Natural Sources ◽  
Glcnac Residue ◽  
Amino Acid Peptide ◽  
Ready Access ◽  
Synthetic Application

The synthetic application of endohexosaminidase enzymes (e.g., Endo A, Endo M, Endo D) promises to allow ready access to a wide variety of defined homogeneous glycoproteins and glycopeptides. The use ofN-glycan oligosaccharides that are activated at the reducing terminus as oxazolines allows their high-yielding attachment to almost any amino acid, peptide, or protein that contains a GlcNAc residue as an acceptor. A wide variety of oxazoline donors are readily available, either by total synthesis or by isolation of the corresponding oligosaccharide from natural sources and then conversion to the oxazoline in water. The synthetic potential of the enzymes is particularly augmented by the production of mutant glycosynthases, the use of which allows the synthesis of a wide variety of glycopeptides and glycoproteins bearing defined homogeneousN-glycan structures.

Protecting-Group-Free Diastereoselective Total Synthesis of (±)-6-epi-Cleistenolide and Chemoenzymatic Synthesis of (-)-6-epi-Cleistenolide

2014 ◽  
Vol 2014 (36) ◽  
pp. 8049-8054 ◽  
Author(s):  
Pankaj S. Mahajan ◽  
Rajesh G. Gonnade ◽  
Santosh B. Mhaske
Keyword(s):  
Total Synthesis ◽  
Chemoenzymatic Synthesis ◽  
Protecting Group

Synthetic Application of Acylnitroso Diels?Alder Derived Aminocyclopentenols: Total Synthesis of (+)-Streptazolin (I).

ChemInform ◽  
2005 ◽  
Vol 36 (21) ◽  
Author(s):  
Fangzheng Li ◽  
Namal C. Warshakoon ◽  
Marvin J. Miller
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Synthetic Application

scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2020 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair Herron ◽  
Shuang Liu ◽  
jin-quan yu
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Pivalic Acid ◽  
Coupling Reactions ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Rapid Construction ◽  
Synthetic Application

The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp<sup>3</sup>)−H/C(sp<sup>2</sup>)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-<i>N</i>-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

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