640-06-2Relevant academic research and scientific papers
Influence of intramolecular hydrogen bonds in the enzyme-catalyzed regioselective acylation of quinic and shikimic acid derivatives
Armesto, Nuria,Fernández, Susana,Ferrero, Miguel,Gotor, Vicente
, p. 5401 - 5410 (2007/10/03)
Selective mono-functionalization of 3-epi, 4-epi-, and 5-epi quinic and shikimic acid derivatives has been accomplished by enzymatic acylation with Candida antarctica lipase A (CAL-A). We propose that the selectivity of this lipase is related to both the
Divergence between the enzyme-catalyzed and noncatalyzed synthesis of 3-dehydroquinate
Bartlett,McLaren,Marx
, p. 2082 - 2085 (2007/10/02)
Synthesis of 1-epi-dehydroquinate, 9, provided an authentic sample of this material and allowed its identification as a minor product in the noncatalyzed rearrangement of enolpyranose 4a to 3-dehydroquinate, 7 (3-DHQ) None of this isomer was detected in the product of the transformation of DAHp, 1 , to 3-DHQ catalyzed by dehydroquinate synthase. This result indicates that the enolpyranose 4a is not released from the enzyme active site prior to rearrangement to 3-DHQ, a possibility suggested previously (Bartlett, P.A.; Satake, K.J. Am. Chem. Soc. 1988, 110, 1628-1630). Enolpyranose 4a was generated in the presence of DHQ synthase; however, the formation of 9 was not diminished, indicating that spontaneous rearrangement is faster than uptake by the enzyme under these conditions. The question remains whether the enzyme takes an active role in catalyzing the rearrangement of 4a to 3-DHQ or simply provides a conformational template to prevent formation of the side product 9.
