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Start Over Topic aldehydes Topic mandelic acids
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1. Asymmetric C 1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids.

Author

Liu Y, Fu Z, Dong H, Zhang J, Mao Y, Zheng M, and Liao C

Subjects
Biocatalysis, Hydroxylation, Benzaldehydes, Stereoisomerism, Aldehydes, Mandelic Acids
Abstract

The development of mild, efficient, and enantioselective methods for preparing chiral building blocks from simple, renewable carbon units has been a long-term goal of the sustainable chemical industry. Mandelate derivatives are valuable pharmaceutical intermediates and chiral resolving agents, but their manufacture relies heavily on highly toxic cyanide. Herein, we report (S)-4-hydroxymandelate synthase (HmaS)-centered biocatalytic cascades for the synthesis of mandelates from benzaldehydes and glycine. We show that HmaS can be engineered to perform R-selective hydroxylation by single-point mutation, empowering the stereodivergent synthesis of both (S)- and (R)-mandelate derivatives. These biocatalytic cascades enabled the production of various mandelate derivatives with high atom economy as well as excellent yields (up to 98 %) and ee values (up to >99 %). This methodology offers an effective cyanide-free technology for greener and sustainable production of mandelate derivatives., (© 2023 Wiley-VCH GmbH.)

Published
2023
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4. Second supplement for the paper chromatographic separation and identification of phenol derivatives and related compounds of biochemical interest, using a 'reference system'

Author

L. Reio

Subjects
Indoles, Catechols, Naphthalenes, Benzoates, Biochemistry, Analytical Chemistry, Nitrophenols, chemistry.chemical_compound, Acetic acid, Phenols, Pyridine, Ehrlich's reagent, Organic chemistry, Indole test, Aldehydes, Chromatography, Phenol, Hippurates, Research, Organic Chemistry, Quinoline, Hippuric acid, Resorcinols, General Medicine, Tryptamines, chemistry, Cinnamates, Benzaldehydes, Reagent, Quinolines, Mandelic Acids
Abstract

Supplementary data are given for the paper-chromatographic investigation of mono-, di- and trihydric phenol derivatives and various compounds of biochemical interest, such as biogenic amines, aromatic and heterocyclic amino acids, hippuric acids, indole derivatives. Some further types of compounds such as alkaloids, hydroxylated quinoline and pyridine derivatives and antibiotics, not dealt with in previous investigations reported earlier in these Reviews, have now been included. The R F values of these compounds in six different solvent systems together with the corresponding colour reactions produced by ten standard reagents have been determined and are presented in 15 tables. Altogether approx. 270 compounds have been investigated and 20 hippuric acid derivatives synthetized. Application of these procedures to the clinical-chemical analysis of urine samples in order to detect metabolic excretion or detoxification products is indicated. The hippuric acid reagent was modified so that it contained p -dimethylamino-cinnamaldehyde in acetic acid anhydride. The Ehrlich reagent was prepared on the basis of p -dimethylaminocinnamaldehyde in hydrochloric acid; the colours produced with this reagent made it possible to differentiate the indole derivatives more distinctly. The relation between the chemical structure of the compounds studied and the R F values and colours produced with the detection reagents, is discussed.

Published
1964

7. Asymmetric C1 Extension of Aldehydes through Biocatalytic Cascades for Stereodivergent Synthesis of Mandelic Acids.

Author

Liu, Yanqiong, Fu, Zunyun, Dong, Haihong, Zhang, Jingxuan, Mao, Yingle, Zheng, Mingyue, and Liao, Cangsong

Subjects
SUSTAINABILITY, ALDEHYDES, CHEMICAL industry, ACIDS, CYANIDES
Abstract

The development of mild, efficient, and enantioselective methods for preparing chiral building blocks from simple, renewable carbon units has been a long‐term goal of the sustainable chemical industry. Mandelate derivatives are valuable pharmaceutical intermediates and chiral resolving agents, but their manufacture relies heavily on highly toxic cyanide. Herein, we report (S)‐4‐hydroxymandelate synthase (HmaS)‐centered biocatalytic cascades for the synthesis of mandelates from benzaldehydes and glycine. We show that HmaS can be engineered to perform R‐selective hydroxylation by single‐point mutation, empowering the stereodivergent synthesis of both (S)‐ and (R)‐mandelate derivatives. These biocatalytic cascades enabled the production of various mandelate derivatives with high atom economy as well as excellent yields (up to 98 %) and ee values (up to >99 %). This methodology offers an effective cyanide‐free technology for greener and sustainable production of mandelate derivatives. [ABSTRACT FROM AUTHOR]

Published
2023
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