1963
DOI: 10.1021/ja00886a019
|View full text |Cite
|
Sign up to set email alerts
|

The Structure and Synthesis of Firefly Luciferin

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

2
112
0

Year Published

1967
1967
2018
2018

Publication Types

Select...
6
3

Relationship

0
9

Authors

Journals

citations
Cited by 235 publications
(114 citation statements)
references
References 4 publications
2
112
0
Order By: Relevance
“…The chemical structure of D-luciferin, isolated from firefly tails, was proposed in 1961 [20] and later confirmed by synthesis (Scheme 1) [21]. The overall yield of D-luciferin 1 from p-anisidine 4 is 9% through nine steps.…”
Section: Synthesis Of D-luciferin From P-anisidinementioning
confidence: 92%
See 1 more Smart Citation
“…The chemical structure of D-luciferin, isolated from firefly tails, was proposed in 1961 [20] and later confirmed by synthesis (Scheme 1) [21]. The overall yield of D-luciferin 1 from p-anisidine 4 is 9% through nine steps.…”
Section: Synthesis Of D-luciferin From P-anisidinementioning
confidence: 92%
“…According to Seto et al, [22] 6-methoxybenzothiazole-2-carboxyamide 10 is prepared from the 4-methoxythioxanilinamide 13 by oxidative cyclization with alkaline K 3 [Fe(CN) 6 ] (Scheme 2). The transformation of compound 10 into the nitrile 11 has been carried out essentially as reported by White et al [21] The preparation of 4-methoxythioxanilinamide 13, according to Seto et al can be carried out in good yields from p-anisidine 4 and carbamoylthiocarbonylthioacetic acid 14. However, this compound is unstable and has to be prepared in situ, as described in detail by Bowie [23].…”
Section: Synthesis Of D-luciferin From 4-methoxythioxanilinamide 13mentioning
confidence: 99%
“…In general, bioluminescence is produced through chemical reactions in which substrates, called luciferins, and enzymes, called luciferases, are involved in the production of light (Shimomura, 2006). Biochemical studies revealed that the firefly luciferin, (4S)-4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid, is structurally identical between P. pyralis and L. cruciata (White et al, 1961;Kishi et al, 1968). It is believed that the luciferin structure is the same among all lampyrid species (Seliger and McElroy, 1964).…”
Section: Fireflies (Lampyridae)mentioning
confidence: 99%
“…The chemical structure of o( --)-luciferin was confirmed by a synthesis involving the condensation of 2-cyano-6-hydroxybenzthiazole and o( --)-cysteine. The condensation product employing the L(+)-cysteine was inoperative in the production of the light burst in the enzyme system (White, McCapra, Field & McElroy, 1961;White, McCapra & Field, 1963).…”
Section: Introductionmentioning
confidence: 99%