Protochlorophyllide

Protochlorophyllide
Names
IUPAC name
Magnesium (21R)-3-(2-carboxyethyl)-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinyl-3,4,23,25-tetradehydrophorbine-23,25-diide
Other names
Monovinyl protochlorophyllide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C35H34N4O5.Mg/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22;/h8,12-14,31H,1,9-11H2,2-7H3,(H3,36,37,38,39,40,41,42);/q;+2/p-2/t31-;/m1./s1
    Key: QBPCOMNNISRCTC-JSSVAETHSA-L
  • CCC1=C(C)C2=[N+]3C1=Cc1c(C)c4C(=O)[C@H](C(=O)OC)C5=C6C(CCC(O)=O)=C(C)C7=[N+]6[Mg--]3(n1c45)n1c(=C7)c(C)c(C=C)c1=C2
Properties
C35H32MgN4O5
Molar mass 612.957 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
The Arabidopsis mutant (FLU), unable to control biosynthesis of protochlorophyllide, glows red in the blue light.

Protochlorophyllide,[1] or monovinyl protochlorophyllide, is an intermediate in the biosynthesis of chlorophyll a. It lacks the phytol side-chain of chlorophyll and the reduced pyrrole in ring D.[2] Protochlorophyllide is highly fluorescent; mutants that accumulate it glow red if irradiated with blue light.[3] In angiosperms, the later steps which convert protochlorophyllide to chlorophyll are light-dependent, and such plants are pale (chlorotic) if grown in the darkness. Gymnosperms, algae, and photosynthetic bacteria have another, light-independent enzyme and grow green in the darkness as well.

  1. ^ KEGG compound database entry [1]
  2. ^ Willows, Robert D. (2003). "Biosynthesis of chlorophylls from protoporphyrin IX". Natural Product Reports. 20 (6): 327–341. doi:10.1039/B110549N. PMID 12828371.
  3. ^ Meskauskiene R, Nater M, Goslings D, Kessler F, op den Camp R, Apel K. FLU: a negative regulator of chlorophyll biosynthesis in Arabidopsis thaliana. Proceedings of the National Academy of Sciences of the United States of America. 2001; 98(22):12826-31 pdf.