Title |
Design and Synthesis of Biotin Analogues Reversibly Binding with Streptavidin
|
---|---|
Published in |
Chemistry - An Asian Journal, March 2015
|
DOI | 10.1002/asia.201500120 |
Pubmed ID | |
Authors |
Tomohiro Yamamoto, Kiyoshi Aoki, Akira Sugiyama, Hirofumi Doi, Tatsuhiko Kodama, Yohei Shimizu, Motomu Kanai |
Abstract |
We synthesized two new biotin analogues, biotin carbonate 5 and biotin carbamate 6. These molecules were designed to reversibly bind with streptavidin by replacing the hydrogen bond donor NH group(s) of biotin's cyclic urea moiety to oxygen. Biotin carbonate 5 was synthesized from L-arabinose (7), which furnishes the desired stereochemistry at the 3,4-cis-dihydroxy groups, in 11% overall yield (10 steps). Synthesis of biotin carbamate 6 was accomplished from L-cysteine-derived chiral aldehyde 33 in 11% overall yield (7 steps). Surface plasmon resonance analysis of water-soluble biotin carbonate analogue 46 and biotin carbamate analogue 47 revealed that KD values of these compounds for binding to streptavidin were 6.7x10-6 M (46) and 1.7x10-10 M (47), respectively. These values were remarkably greater than that of biotin (KD = 10-15 M), and thus indicate the importance of the nitrogen atoms of biotin's cyclic urea motif for the strong binding between biotin and streptavidin. |
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