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Design and Synthesis of Biotin Analogues Reversibly Binding with Streptavidin

Overview of attention for article published in Chemistry - An Asian Journal, March 2015
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  • In the top 25% of all research outputs scored by Altmetric
  • Good Attention Score compared to outputs of the same age (79th percentile)
  • High Attention Score compared to outputs of the same age and source (93rd percentile)

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2 X users
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2 patents
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1 Facebook page

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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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Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 24 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 24 100%

Demographic breakdown

Readers by professional status Count As %
Student > Bachelor 6 25%
Student > Master 4 17%
Professor > Associate Professor 3 13%
Student > Ph. D. Student 3 13%
Other 2 8%
Other 2 8%
Unknown 4 17%
Readers by discipline Count As %
Chemistry 13 54%
Agricultural and Biological Sciences 3 13%
Pharmacology, Toxicology and Pharmaceutical Science 1 4%
Biochemistry, Genetics and Molecular Biology 1 4%
Business, Management and Accounting 1 4%
Other 2 8%
Unknown 3 13%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 8. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 21 March 2023.
All research outputs
#4,519,282
of 24,417,958 outputs
Outputs from Chemistry - An Asian Journal
#323
of 5,844 outputs
Outputs of similar age
#52,224
of 262,143 outputs
Outputs of similar age from Chemistry - An Asian Journal
#5
of 75 outputs
Altmetric has tracked 24,417,958 research outputs across all sources so far. Compared to these this one has done well and is in the 81st percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 5,844 research outputs from this source. They receive a mean Attention Score of 1.8. This one has done particularly well, scoring higher than 94% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 262,143 tracked outputs that were published within six weeks on either side of this one in any source. This one has done well, scoring higher than 79% of its contemporaries.
We're also able to compare this research output to 75 others from the same source and published within six weeks on either side of this one. This one has done particularly well, scoring higher than 93% of its contemporaries.