Nitrogen- and Phosphorus-Containing Compounds

Question 1

amino acid configuration in all eukaryotes

Answer 1

L-amino acids

Question 2

stereochemistry in all amino acids in eukaryotes, except cysteine

Answer 2

(S) sterochemistry

Question 3

generates an amino acid from an aldehyde which is mixed with ammonium chloride (NH4Cl) and potassium cyanide (KCN); ammonia attacks the carbonyl, generating an imine; the imine is attacked by the cyanide, generating an aminonitrile; the aminonitrile is hydrolyzed by two equivalents of water, generating an amino acid

Answer 3

Strecker synthesis

Question 4

Answer 4

Strecker synthesis

Question 5

generates an amino acid from potassium phthalimide, diethyl bromomalonate, and an alkyl halide using two SN2 reactions, hydrolysis, and decarboxylation; phthalimide attacks the diethyl bromomalonate, generating a phthalimidomalonic ester; the phthalimidomalonic ester attacks an alkyl halide, adding an alkyl group to the ester; the product is hydrolyzed, creating phthalic acid (with two carboxyl groups) and converting the esters into carboxylic acids; one carboxylic acid of the resulting 1,3-dicarbonyl is removed by decarboxylation

Answer 5

Gabriel synthesis

Question 6

Answer 6

Gabriel synthesis

Question 7

source of phosphorus; a buffered mixture of hydrogen phosphate (HPO4^2-) and dihydrogen phosphate (H2PO4-)

Answer 7

inorganic phosphate (P(i)) (phosphate group)

Question 8

contains phosphorus in phosphodiester bonds

Answer 8

backbone of DNA

Question 9

is released in the formation of phosphodiester bonds; can then be hydrolyzed to two inorganic phosphates

Answer 9

pyrophosphate (PP(i), P2O7^4-)

Question 10

relative energy level of phosphate bonds because of large negative charges in adjacent phosphate groups and resonance stabilization

Answer 10

high energy

Question 11

carbon-containing compounds that also have phosphate groups;

e.g. nucleotide triphosphates (like ATP or GTP) and DNA

Answer 11

organic phosphates

Question 12

wide variety allows phosphoric acid to act as a buffer over a large range of pH values

Answer 12

phosphoric acid has 3 hydrogens, each with a unique pKa