Efficient One-Step Conversion of Primary Aliphatic Amines into Primary Alcohols:  Application to a Model Study for the Total Synthesis of (±)-Scopadulin

2000 ◽  
Vol 2 (18) ◽  
pp. 2893-2895 ◽  
Author(s):  
S. M. Abdur Rahman ◽  
Hiroaki Ohno ◽  
Naoyoshi Maezaki ◽  
Chuzo Iwata ◽  
Tetsuaki Tanaka
Keyword(s):  
Total Synthesis ◽  
Aliphatic Amines ◽  
Primary Alcohols ◽  
Model Study ◽  
One Step ◽  
Primary Aliphatic Amines

scholarly journals The dye-linked alcohol dehydrogenase of Rhodopseudomonas acidophila. Comparison with dye-linked methanol dehydrogenases

1978 ◽  
Vol 169 (3) ◽  
pp. 677-686 ◽  
Author(s):  
C W Bamforth ◽  
J R Quayle
Keyword(s):  
Alcohol Dehydrogenase ◽  
Aliphatic Amines ◽  
Primary Alcohols ◽  
Ph Optimum ◽  
Rhodopseudomonas Acidophila ◽  
Wide Range ◽  
The Stability ◽  
Phenazine Methosulphate ◽  
Primary Aliphatic Amines

1. A dye-linked alcohol dehydrogenase was purified 20-fold from extracts of Rhodopseudomonas acidophila 10050 grown anaerobically in the light on methanol/HCO3-. 2. The enzyme resembled many previously reported methanol dehydrogenases from other methylotrophic organisms in coupling to phenazine methosulphate, requiring ammonia as an activator, possessing a pH optimum of 9 and a mol.wt. of approx. 116000. In many other respects the enzyme showed singular properties. 3. The stability of the enzyme under various conditions of temperature and pH was studied. 4. Primary aliphatic amines containing up to nine carbon atoms (the longest tested) were better activators than ammonia. 5. A wide range of primary alcohols and aldehydes served as substrates, with apparent Km values ranging from 57 mM for methanol to 6 micron for ethanol. 6. O2 was an inhibitor competitive with respect to the alcohol substrate. In the presence of O2, apparent Km values of 145 mM were recorded for methanol. 6. Cyanide and alphaalpha'-bipyridine were inhibitors competitive with respect to the amine activator. 7. The properties of the enzyme from Rhodopseudomonas acidophila are compared with those of similar enzymes from other organisms, and implications of the salient differences are discussed.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Pd‐Catalyzed Regio‐ and Stereoselective sp 3 C−H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications

2021 ◽  
Vol 2021 (7) ◽  
pp. 1136-1145
Author(s):  
Hyeonbin Ha ◽  
Ho Jeong Choi ◽  
Hahyoun Park ◽  
Yunyeong Gwon ◽  
Jiin Lee ◽  
...  
Keyword(s):  
Aliphatic Amines ◽  
Mechanistic Studies ◽  
Primary Aliphatic Amines

A novel, one-step method for the conversion of primary alcohols into carbamate-protected amines

2002 ◽  
Vol 43 (21) ◽  
pp. 3887-3890 ◽  
Author(s):  
Michael R. Wood ◽  
June Y. Kim ◽  
Kathy M. Books
Keyword(s):  
Primary Alcohols ◽  
Step Method ◽  
One Step

Oxidation of primary aliphatic amines with sodium perborate

1989 ◽  
Vol 30 (47) ◽  
pp. 6495-6496 ◽  
Author(s):  
Walter W Zajac ◽  
Michael G Darcy ◽  
Amador P Subong ◽  
John H Buzby
Keyword(s):  
Aliphatic Amines ◽  
Sodium Perborate ◽  
Primary Aliphatic Amines

Chemoenzymatic Formal Total Synthesis of Pancratistatin from Narciclasine-Type Compounds via Myers Transposition: Model Study for a Short Conversion of Narciclasine to Pancratistatin

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2896-2900 ◽  
Author(s):  
Ringaile Lapinskaite ◽  
Mukund Ghavre ◽  
Chelsea Rintelmann ◽  
Korey Bedard ◽  
Helen Dela Paz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Recombinant Strain ◽  
Optical Purity ◽  
Allylic Alcohol ◽  
Formal Synthesis ◽  
Toluene Dioxygenase ◽  
Single Isomer ◽  
Model Study ◽  
New Compounds ◽  
Subsequent Opening

A formal total synthesis of pancratistatin was accomplished by conversion of advanced intermediates, used in the synthesis of narciclasine, to pancratistatin precursors via Myers’ reductive transposition as the key strategic step. The synthesis began with the whole cell fermentation of m-dibromobenzene with JM109(pDTG601a), a recombinant strain that over-expresses toluene dioxygenase, which provided the corresponding cis-dihydrodiol 16 as a single isomer with complete optical purity. The key reductive transposition of the allylic alcohol 8a to olefin 9a allowed for further installation of the C-1/C-2 trans-diol, ­required for the pancratistatin scaffold, through the introduction of a cyclic sulfate and its subsequent opening. The formal synthesis of pancratistatin was accomplished in 14 steps (12 operations) from commercially available m-dibromobenzene. Experimental and spectral data are provided for all new compounds.

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