- Synthesis of l-2,3-trans-3,4-cis-dihydroxyproline building blocks for peptide synthesis
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L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O- isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.
- Weir, Claudette A.,Taylor, Carol M.
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Read Online
- Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline
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Genome mining for novel Fe(II)/α-ketoglutarate-dependent dioxygenases (αKGDs) to expand the enzymatic repertoire in the oxidation of l-proline is reported. Through clustering of proteins, we predicted regio- and stereoselectivity in the hydroxylation reaction and validated this hypothesis experimentally. Two novel byproducts in the reactions with enzymes from Bacillus cereus and Streptomyces sp. were isolated, and the structures were determined to be a 3,4-epoxide and a 3,4-diol, respectively. The mechanism for the formation of the epoxide was investigated by performing an 18O-labeling experiment. We propose that the mechanism proceeds via initial cis-3-hydroxylation followed by ring closure. A biocatalytic step was run on subgram quantities of starting material without any significant optimization of the conditions. However, the substrate concentration was 40-fold higher than the usual reported titers for recombinant P450-mediated hydroxylations, showing the synthetic potential of αKGDs on a preparative scale.
- Dussauge, Solene,Moore, Charles,Snajdrova, Radka,Tassano, Erika,Vargas, Alexandra
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supporting information
(2022/02/09)
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- Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles
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Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.
- Smart, Tristan J.,Hamed, Refaat B.,Claridge, Timothy D.W.,Schofield, Christopher J.
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supporting information
(2019/11/26)
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- Structural essentials for β-: N -acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids
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This paper explores the computer modelling aided design and synthesis of β-N-acetylhexosaminidase inhibitors along with their applicability to human disease treatment through biological evaluation in both an enzymatic and cellular setting. We investigated the importance of individual stereocenters, variations in structure-activity relationships along with factors influencing cell penetration. To achieve these goals we modified nitrogen heterocycles in terms of ring size, side chains present and ring nitrogen derivatization. By reducing the inhibitor interactions with the active site down to the essentials we were able to determine that besides the established 2S,3R trans-relationship, the presence and stereochemistry of the CH2OH side chain is of crucial importance for activity. In terms of cellular penetration, N-butyl side chains favour cellar uptake, while hydroxy- and carboxy-group bearing sidechains on the ring nitrogen retarded cellular penetration. Furthermore we show an early proof of principle study that β-N-acetylhexosaminidase inhibitors can be applicable to use in a potential anti-invasive anti-cancer strategy.
- Glawar,Martínez,Ayers,Hollas,Ngo,Nakagawa,Kato,Butters,Fleet,Jenkinson
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p. 10371 - 10385
(2016/11/18)
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- Diversity oriented concise asymmetric synthesis of azasugars: A facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine
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Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields.
- Gajare, Vikas S.,Khobare, Sandip R.,Datrika, Rajender,Reddy, K. Srinivas,Rajana, Nagaraju,Kumar, Sarvesh,Venkateswara Rao,Syam Kumar
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supporting information
p. 6659 - 6663
(2016/01/28)
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- Asymmetric synthesis of d -proline, d -pipecolic acid, (2 R,3 S,4 R)-3,4-dihydroxyproline, and 1,4-Dideoxy-1,4-imino- d -talitol from a Common Precursor
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Methodology involving stereoselective aza-Michael addition and ring-closing metathesis as key steps has been developed for the preparation of (2R)-pipecolic acid, (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline, and the known glycosidase inhibiting azasugar 1,4-dideoxy-1,4-imino-d-talitol from a common starting material namely (R)-cyclohexylideneglyceraldehyde in good overall yields. Georg Thieme Verlag Stuttgart New York.
- Chattopadhyay, Shital K.,Mukherjee, Jyoti Prasad
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p. 2481 - 2488
(2014/10/15)
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- Asymmetric Synthesis of d -Proline, d -Pipecolic Acid, (2 R,3 S,4 R)-3,4-Dihydroxyproline, and 1,4-Dideoxy-1,4-imino- d -talitol from a Common Precursor
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Methodology involving stereoselective aza-Michael addition and ring-closing metathesis as key steps has been developed for the preparation of (2R)-pipecolic acid, (2R)-proline, (2R,3S,4R)-3,4-dihydroxyproline, and the known glycosidase inhibiting azasugar 1,4-dideoxy-1,4-imino-d-talitol from a common starting material namely (R)-cyclohexylideneglyceraldehyde in good overall yields.
- Chattopadhyay, Shital K.,Mukherjee, Jyoti Prasad
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p. 2481 - 2488
(2015/12/26)
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- Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases
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We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to L-proline and L-pipecolinic acid, we found that 3,4-dehydro-L-proline, L-azetidine-2-carboxylic acid, cis-3-hydroxy-L-proline, and L-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-L-proline, cis-3-hydroxy-L-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-L-proline.
- Hara, Ryotaro,Uchiumi, Naoko,Okamoto, Naoko,Kino, Kuniki
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p. 1384 - 1388
(2015/07/20)
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- Stereoselective synthesis of 3,4-dihydroxylated prolines and prolinols starting from L -tartaric acid
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A straightforward and stereoselective synthesis of 3,4-dihydroxyprolines and 3,4-dihydroxyprolinols is described. The key reaction in this synthesis is a protective group-controlled diastereoselective cyanation of a chiral acyliminium intermediate derived from l-tartaric acid. Methanolysis of the obtained cyanolactam gave methyl 3,4-dihydroxypyroglutamate that was converted to 3,4-dihydroxyproline and 3,4-dihydroxyprolinol by reduction of the lactam carbonyl and ester groups in a stepwise manner.
- Oba,Koguchi,Nishiyama
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p. 237 - 243
(2014/02/14)
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- Stereospecific cyclization strategies for α,ε-dihydroxy-β-amino esters: Asymmetric syntheses of imino and amino sugars
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A range of biologically significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3 R,4 S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has bee
- Davies, Stephen G.,Foster, Emma M.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
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p. 9686 - 9698
(2015/01/09)
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- The conversion of pentoses to 3,4-dihydroxyprolines
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The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproline was synthesized from L-arabinose in 10 steps and 31% overall yield. The same series of reactions was employed to convert L-xylos
- Taylor, Carol M.,Jones, Chantelle E.,Bopp, Kristin
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p. 9611 - 9617
(2007/10/03)
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- Total synthesis of 3,4-dihydroxyprolines, D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester
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The Henry reaction between D-glyceraldehyde and ethyl nitroacetate allowed the practical development of a diastereoselective synthesis of 3,4,5-trihydroxy-2-nitropentanoic acid esters, which were reduced to polyoxamic acids, which were used in a new diastereoselective synthesis of 3,4-dihydroxyprolines and new enantioselective syntheses of D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester.
- Soengas, Raquel G.,Estevez, Juan C.,Estevez, Ramon J.
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p. 3955 - 3963
(2007/10/03)
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- Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)
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cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.
- Garcia, Ariel Lázaro L.,Correia, Carlos Roque D.
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p. 1553 - 1557
(2007/10/03)
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- Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars
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A general strategy is proposed, wherein a pentose sugar γ-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3, 4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3, 4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl- 3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.
- Taylor, Carol M.,Taylor, Carol M.,Barker, William D.,Weir, Claudette A.,Park, Jae H.
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p. 4466 - 4474
(2007/10/03)
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- Facile synthesis of 3,4-dihydroxyprolines as an application of the L- threonine aldolase-catalyzed aldol reaction
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A new facile synthesis of 3,4-dihydroxyprolines was attained by taking advantage of the L-threonine aldolase, which catalyzes the aldol condensation reaction of aldehydes with glycine affording β-hydroxy-α-L-amino acids.
- Fujii, Mikio,Miura, Tsuyoshi,Kajimoto, Tetsuya,Ida, Yoshiteru
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p. 1046 - 1048
(2007/10/03)
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- A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline 1,4-Dideoxy-1,4-imino-L-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-L-iditol
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The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47 percent and 60 percent overall yield from 2-azido-2-deoxy-L-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51 percent and 53 percent overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.
- Lee, Byong Won,Jeong, Ill-Yun,Yang, Min Suk,Choi, Sang Uk,Park, Ki Hun
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p. 1305 - 1309
(2007/10/03)
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- A novel method for deprotection of N-9-phenylfluoren-9-yl group using iodine catalyst: Simple synthesis of (2S, 3R, 4R)-3,4-dihydroxyproline
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Iodine was found to be an efficient catalyst for the deprotection of the N-phenylfluoren-9-yl (Pf) group in tertiary amine and promote an intramolecular amination. A facile and economical synthesis of (2S,3R,4R)- 3,4-dihydroxyproline was accomplished via iodine promoted cyclization and deprotection.
- Kim, Jin Hyo,Lee, Woo Song,Yang, Min Suk,Lee, Sang Gyeong,Park, Ki Hun
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p. 614 - 616
(2007/10/03)
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- Synthesis of (2S, 3R, 4S), (2S, 3S, 4R)-epoxyprolines and aminohydroxyprolines
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25, 3R, 4S- and 25, 38, 4R-epoxy-L-prolines were synthesised from trans- 4-hydroxy-L-proline. Assignment of the stereochemical configurations of the epoxy prolines was achieved by n.O.e. studies and chemical correlation. The synthetic utility of the protected epoxides was investigated briefly by ring opening with NAN3, followed by deprotection to give aminohydroxy prolines.
- Robinson, J. Kenneth,Lee, Victor,Claridge, Timothy D. W.,Baldwin, Jack E.,Schofield, Christopher J.
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p. 981 - 996
(2007/10/03)
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- Straightforward Synthesis of Pyrrolidine Glycosidase Inhibitors via Asymmetric Hetero-Diels-Alder Reaction
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Base-catalysed rearrangement of the oxazine-carboxylate 8, obtained from pentadienoic acid 4 by asymmetric hetero-Diels-Alder reaction followed by simple chemical transformations, led to the protected trihydroxy-proline 9. Using various reduction conditions, the potent glycosidase inhibitors 1,4-dideoxy-1,4-imino-D-lyxitol D-1 and 1,4-dideoxy-1,4-imino-L-ribitol L-2 were obtained.
- Defoin, Albert,Sifferlen, Thierry,Streith, Jacques
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p. 1294 - 1296
(2007/10/03)
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- Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate
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A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro
- Pohlit, Adrian M.,Correia, Carlos Roque D.
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p. 2321 - 2325
(2007/10/03)
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- Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline
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Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon.
- Zanardi, Franca,Battistini, Lucia,Nespi, Marika,Rassu, Gloria,Spanu, Pietro,Cornia, Mara,Casiraghi, Giovanni
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p. 1167 - 1180
(2007/10/03)
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- (±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams
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Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th
- Behr,Defoin,Mahmood,Streith
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p. 1166 - 1177
(2007/10/02)
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- Substrate specificity of proline 4-hydroxylase: Chemical and enzymatic synthesis of 2S,3R,4S-epoxyproline
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The substrate specificity of L-proline 4-hydroxylase, a 2-oxoglutarate dependent dioxygenase from Streptomyces griseoviridus P8648, was investigated. Preliminary assays measuring turnover of 2-oxyglutarate indicated 3,4-dehydro-L-proline was an efficient
- Baldwin,Field,Lawrence,Lee,Robinson,Schofield
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p. 4649 - 4652
(2007/10/02)
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- Synthesis of (2R,3S,4R)-3,4-Dihydroxy-2-hydroxymethylpyrrolidine and (2S,3R,4S,5S)-3,4-dihydroxy-2,5-dihydroxymethylpyrrolidine from (R)-Serine and D-Ribonolactone
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(2R,3S,4R)-3,4-Dihydroxy-2-hydroxymethylpyrrolidine derivative (9,10) and (2S,3R,4S,5S)-3,4-dihydroxy-2,5-dihydroxymethylpyrrolidine derivatives (16,17) were synthesized stereoselectively from (R)-serine and D-ribonolactone, respectively.
- Ikota, Nobuo
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p. 2035 - 2050
(2007/10/02)
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- Stereoselective synthesis of (+)-1,8-Di-epi- and (-)-1-epi-swainsonine from an (S)-pyroglutamic acid derivative
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(+)-1,8-Di-epi-swainsonine (15) and (-)-1-epi-swainsonine (17) were synthesized stereoselectively from an (S)-pyroglutamic acid derivative (1a). A (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine derivative (6a) was prepared by cis-dihydroxylation of a
- Ikota
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p. 1717 - 1721
(2007/10/02)
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- DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES FOR THE SYNTHESIS OF POLYHYDROXYPYRROLIDINES AS POTENTIAL ENZYMATIC INHIBITORS
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Tosyl and benzyl azomethine ylides generated from the corresponding aziridines under thermal and photochemical conditions, were trapped by dipolar cycloaddition reaction with vinylene carbonate.The methoxycarbonyl group in the pyrrolidines obtained was re
- Hassan, Mohamed E.
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- Synthesis of (2S, 3R, 4R)-3,4-Dihydroxyproline from 2,5-Dibromo-2,5-dideoxy-D-xylono- or -lyxono-1,4-lactone
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(2S, 3R, 4R)-3,4-dihydroxyproline (8) has been prepared in three steps from 2,5-dibromo-2,5-dideoxy-D-xylono-1,4-lactone (1).Azidolysis of 1 gave the 2-azido-5-bromo-2,5-dideoxy-D-lyxono-1,4-lactone (2), which by hydrogenolysis and hydrolysis gave 8.Azidolysis of 2,5-dibromo-2,5-dideoxy-D-lyxono-1,4-lactone (9) and 2,3-anhydro-5-bromo-5-deoxy-D-lyxono-1,4-lactone (10) also gave 2.Azidolysis of 10 in the absence of a proton donor led to degradation with evolution of nitrogen.
- Bols, Mikael,Lundt, Inge
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p. 298 - 300
(2007/10/02)
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- Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid
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Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.
- Arakawa,Yoshifuji
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p. 2219 - 2224
(2007/10/02)
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- SYNTHESIS OF CHIRAL PYRROLIDINE AND PIPERIDINE GLYCOSIDASE INHIBITORS
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There is disclosed a novel method for the syntheses of chiral pyrrolidines and piperidines by the intramolecular ring closure of anomeric mixtures of 4-amino- and 5-amino-2-trifluoromethanesulfonates of methyl furanosides. The novel method preferably prov
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- Synthesis of homochiral β-hydroxy-α-aminoacids [2S,3R,4R)-3, 4-dihydroxyproline and (2S,3R,4R)-3,4-dihydroxypipecolic acid] and of 1,4-dideoxy-1,4-imino-D-arabinitol [DAB1] and fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol]
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Efficient syntheses from diacetone glucose of 1,4-dideoxy-1, 4-imino-D-arabinitol, (2S,3R,4R)-3,4-dihydroxyproline, fagomine [1,5-imino-1,2,5-trideoxy-D arabino-hexitol], and (2S,3R,4R)-3,4)-3,4-dihydroxpipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides are reported.
- Fleet,Witty
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p. 119 - 136
(2007/10/02)
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- Ketene Dithioacetals as 1,3-Dipolarophiles. Applications to the Synthesis of Cyclic Amino Acids
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Intramolecular azide cycloaddition reactions of ketene dithioacetals provide a new route to cyclic amino acids and a stereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyproline (14) based on this methodology is described.
- Moss, William O.,Bradbury, Robert H.,Hales, Neil J.,Gallagher, Timothy
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- POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES: SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE
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The use of readily available sugar lactones in the synthesis of polyhydroxylated pyrrolidines is illustrated by the preparation of the glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-glucitol from D-galactonolactone and by the conversion of D-gulonolactone into 1,4-dideoxy-1,4-imino-D-allitol, 1,4-dideoxy-1,4-imino-D-ribitol, and (2S,3R,4S)-3,4-dihydroxyproline.
- Fleet, George W. J.,Son, Jong Chan
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p. 2637 - 2648
(2007/10/02)
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- THE SYNTHESIS OF POLYHYDROXYLATED AMINO ACIDS FROM GLUCURONOLACTONE: ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
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The potential of D-glucuronolactone for the synthesis of polyhydroxylated amino acids is illustrated by the enantiospecific syntheses of 2S,3R,4R,5S-trihydroxypipecolic acid, 2R,3R,4R,5S-trihydroxypipecolic acid and 2R,3R,4R-dihydroxyproline.
- Bashyal, Bharat P.,Chow, Hak-Fun,Fellows, Linda E.,Fleet, George W. J.
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p. 415 - 422
(2007/10/02)
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- Synthesis of (2R,3S,4R)-3,4-Dihydroxyproline from D-Ribonolactone; an Approach to the Synthesis of Polyfunctionalised D-Amino Acids from Sugar Lactones. X-Ray Molecular Structures of 2-Azido-3,4-O-(R)-benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-Azido-2-deoxy-D-ribono-1,4-lactone, and ...
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A general approach to the synthesis of polyfunctionalised amino acids from sugar lactones, in wich nucleophilic displacement by azide ion of O-trifluoromethanesulphonyl esters adjacent to the lactone carbonyl is the key step, is discussed and is exemplified by the synthesis of the D-amino acid (2R,3S,4R)-3,4-dihydroxyproline from d-ribonolactone; unexpectedly, displacement of a triflate by azide in the C-2 position of ribonolactone occurs with retention of configuration.The X-ray crystal structures of 2-azido-3,4-O-(R)-benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-azido-2-deoxy-D-ribono-1,4-lactone, and (2R,3S,4R)-3,4-dihydroxyproline are reported.I.r. spectroscopy does not discriminate reliably between 1,4-and 1,5-lactones, and X-ray crystallography is necessary to provide reliable structural information in this area.
- Baird, Peter D.,Dho, Jonathan C.,Fleet, George W. J.,Peach, Josephine M.,Prout, Keith,Smith, Paul W.
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p. 1785 - 1792
(2007/10/02)
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- SYNTHESIS OF 2R,3S,4R-DIHYDROXYPROLINE FROM D-RIBONOLACTONE
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A synthesis of 2R,3S,4R-dihydroxyproline is described in which an azide is introduced into C-2 position of D-ribonolactone with retention of configuration.
- Dho, J. C.,Fleet, G. W. J.,Peach, J. M.,Prout, K.,Smith, P. W.
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p. 3203 - 3204
(2007/10/02)
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- EFFICIENT SYNTHESES OF NATURALLY OCCURRING 3,4-DIHYDROXYPROLINES: ELECTROPHILE-MEDIATED LACTONIZATION OF 2-AMINO-3-HYDROXY-4-PENTENOIC ACID DERIVATIVES
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Stereospecific conversion of β-hydroxyallylglycine derivatives into (2S,3R,4R)1 and (2S,3S,4S)2 via halo- or mercuri-lactonization has been described.
- Ohfune, Yasufumi,Kurokawa, Natsuko
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p. 5307 - 5308
(2007/10/02)
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- Synthesis of Two Naturally Occuring Diastereomeric Dihydroxyprolines: 2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline and 2,3-cis-3,4-trans-3,4-Dihydroxy-L-proline
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Starting from 2-pyrrolecarboxylic acid the N-Boc derivative 6 is resolved into its optically active constituents by crystalisation with R(+)-1-(4-nitrophenyl)ethaneamin.The N-tosyl-3,4-dehydro-L-proline methyl ester (L-7) derived from this is converted by
- Kahl, Jens-Uwe,Wieland, Theodor
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p. 1445 - 1450
(2007/10/02)
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