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- Title
Design and Synthesis of Biotin Analogues Reversibly Binding with Streptavidin.
- Authors
Yamamoto, Tomohiro; Aoki, Kiyoshi; Sugiyama, Akira; Doi, Hirofumi; Kodama, Tatsuhiko; Shimizu, Yohei; Kanai, Motomu
- Abstract
Two new biotin analogues, biotin carbonate 5 and biotin carbamate 6, have been synthesized. These molecules were designed to reversibly bind with streptavidin by replacing the hydrogen-bond donor NH group(s) of biotin's cyclic urea moiety with 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 (over 10 steps). Synthesis of biotin carbamate 6 was accomplished from L-cysteine-derived chiral aldehyde 33 in 11 % overall yield (over 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 6.7×10−6 M and 1.7×10−10 M, respectively. These values were remarkably greater than that of biotin ( KD=10−15 M), and thus indicate the importance of the nitrogen atoms for the strong binding between biotin and streptavidin.
- Subjects
CHEMICAL synthesis; BIOTIN; STREPTAVIDIN; STEREOCHEMISTRY; HYDROGEN bonding
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 4, p1071
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201500120