Protease-catalyzed synthesis of disaccharide amino acid esters in organic media

Park, Oh-Jin; Jeon, Gyu-Jong; Yang, Ji‐Won

doi:10.1016/s0141-0229(99)00040-x

Cited by 30 publications

(9 citation statements)

References 35 publications

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“…Finally, sugar-amino acid conjugates have also been prepared by enzymatic synthesis in pyridine using commercial protease, Optimase M-440. 133 Benzotriazole methodology offers an advantage for the synthesis of enantiopure O-(protected a-aminoacyl)sugars with reaction times of ca. 15 minutes.…”

Section: O-(aminoacyl)sugar Conjugatesmentioning

confidence: 99%

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Katritzky¹,

Angrish²,

Todadze³

2009

Synlett

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N-(Protected a-aminoacyl)benzotriazoles are efficient intermediates for N-and O-aminoacylation. These intermediates enable fast preparations of biologically relevant peptides and peptide conjugates in high yields and purity, under mild reaction conditions, with full retention of the original chirality. The developed methodology allows simple solution-and solid-phase preparative techniques to generate complex peptides and peptide conjugates and serves as a platform for generating diverse medicinal chemistry building block libraries involving amino acid and heterocyclic moieties crucial for drug development.

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Section: O-(aminoacyl)sugar Conjugatesmentioning

confidence: 99%

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Katritzky¹,

Angrish²,

Todadze³

2009

Synlett

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“…[18] Furthermore, Park et al obtained trehalose 3,6 0 -diester from trehalose by protease from Bacillus lichenformis. [20] We reported the synthesis of 2-O-vinyl adipoyl-D-galactose by protease from Streptomyces sp. in DMF/DMSO mixed solvent.…”

Section: Enzymatic Synthesis Of 2-o-vinyl Adipoyl D-fucose (2vdf) Andmentioning

confidence: 99%

Chemoenzymatic Synthesis of Fucose‐ or Rhamnose‐Branched Polymer

Raku

Tokiwa

2003

Macromolecular Bioscience

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Abstract6‐Deoxy sugars having only secondary alcohols, namely, D‐fucose, L‐fucose, and L‐rhamnose, were regioselectively esterified with divinyl adipate by enzymes. The compounds 2‐O‐vinyl adipolyl D‐fucose and 2‐O‐vinyl adipolyl L‐fucose were effectively produced in dimethylformamide by protease from Bacillus subtilis and Streptomyces griseus. Furthermore, 4‐O‐vinyl adipolyl L‐rhamnose was effectively produced in pyridine by lipase from Pseudomonas sp. Each polymerizable sugar ester was polymerized by 1,1′‐azoisobutyronitrile to give polymers having a number average molecular weight of 5 000–14 000. Part of the chemoenzymatic synthesis of poly(6‐deoxy sugars).magnified imagePart of the chemoenzymatic synthesis of poly(6‐deoxy sugars).

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“…Lipases are structurally well conditioned to perform in such media and are the most used enzymes for sugar ester synthesis. Proteases have been used as well (Park et al 1999;Tokiwa et al 1999;Kennedy et al 2006), being in this case mandatory to increase the stabilization of the enzyme to withstand the harsh conditions of reaction in nonconventional media; therefore proteases for sugar esters are usually used in immobilized form (Ferreira et al 2002;Plou et al 2002;Pedersen et al 2003).…”

Section: Upgrading By Enzymatic Esterificationmentioning

confidence: 99%

“…Likewise, low yields have been obtained in the synthesis of lactose esters when using proteases as catalysts (Park et al 1999;Wu et al 2004). Further developments in biocatalyst and medium engineering are still required for making the enzymatic synthesis of lactose esters commercially viable.…”

Section: Upgrading By Enzymatic Esterificationmentioning

confidence: 99%

Whey upgrading by enzyme biocatalysis

Illanes¹

2011

Electro Journal of Biotech

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Whey is a co-product of processes for the production of cheese and casein that retains most of the lactose content in milk. World production of whey is estimated around 200 million tons per year with an increase rate of about 2%/per year. Milk production is seasonal, so surplus whey is unavoidable. Traditionally, whey producers have considered it as a nuisance and strategies of whey handling have been mostly oriented to their more convenient disposal. This vision has been steadily evolving because of the upgrading potential of whey major components (lactose and whey proteins), but also because of more stringent regulations of waste disposal. Only the big cheese manufacturing companies are in the position of implementing technologies for their recovery and upgrading, so there is a major challenge in incorporating medium and small size producers to a platform of whey utilization, conciliating industrial interest with environmental protection within the framework of sustainable development. Within this context, among the many technological options for whey upgrading, transformation of whey components by enzyme biocatalysis appears as prominent. In fact, enzymes are green catalysts that can perform a myriad of transformation reactions under mild conditions and with strict specificity, so reducing production costs and environmental burden. This review pretends to highlight the impact of biocatalysis within a platform of whey upgrading. Technological options are shortly reviewed and then an in-depth and critical appraisal of enzyme technologies for whey upgrading is presented, with a special focus on newly developed enzymatic processes of organic synthesis, where the added value is high, being then a powerful driving force for industrial implementation.

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Protease-catalyzed synthesis of disaccharide amino acid esters in organic media

Cited by 30 publications

References 35 publications

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

Chemoenzymatic Synthesis of Fucose‐ or Rhamnose‐Branched Polymer

Whey upgrading by enzyme biocatalysis

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