10 Nitrogen- and Phosphorous-Containing Compounds Flashcards Preview

MCAT Organic Chemistry Review > 10 Nitrogen- and Phosphorous-Containing Compounds > Flashcards

Flashcards in 10 Nitrogen- and Phosphorous-Containing Compounds Deck (11)
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1
Q

properties

A
alpha carbon is a chiral (stereogenic) center
except glycine (R group is H)

optically active; all L-isomers

amphoteric molecules

zwitterions in neutral solution (protonated amino group, deprotonated carboxyl group)

2
Q

nonpolar, nonaromatic R group characteristics

A

saturated hydrocarbons

alanine
valine
leucine
isoleucine
glycine
proline
methionine
3
Q

aromatic R group characteristics

A

tryptophan
phenylalanine
tyrosine

4
Q

polar R group characteristics

A

terminal groups are usually O, N, or S

serine
threonine
asparagine
glutamine
cysteine
5
Q

negatively charged (acidic) R group characteristics

A

terminal carboxylate anions

aspartic acid
glutamic acid

6
Q

positively charged (basic) R group characteristics

A

protonated amino group (in R group)

arginine
lysine
histidine

7
Q

peptide bond

A

condensation reaction between amino acids

8
Q

polypeptides

A

result of peptide bond

base units of proteins

9
Q

Strecker synthesis

A

aldehyde, NH4Cl, KCN
can generate both L- and D-amino acids (racemic mixtures)
starts with planar carbonyl-containing compound

Step 1: aminonitrile generated from aldehyde/ketone
Step 2: amino acid generated from aminonitrile

10
Q

Gabriel (malonic-ester) synthesis

A

amino acid generated from phtalamide and diethylbromomalonate

2 SN2 reactions
1 hydrolysis
1 decarboxylation

starts with planar molecule –> racemic mixture (L- and D- amino acids generated)

11
Q

phosphoric acid

A

forms the high-energy bonds that carry energy in ATP

  • phosphate group
  • inorganic phosphate (Pi)

at physiological pH: HPO4(2-) and H2PO4(-)

energy-carrying nucleotide phosphates
backbone of DNA in phosphodiester bonds linking sugar moieties of the nucleotides

excellent buffer (3 hydrogens with pKa values than span nearly the entire pH scale = 2.15, 7.20, 12.52)