Glycine has the molecular formula C2H5O2N. If ten glycines are linked linearly by peptide (condensation) reactions to form an oligomer, what is the correct overall molecular formula?

Biochemistry Structure and Properties of Peptides Difficulty: Medium
Choose an option
  • A
    C20H50O20N10
  • B
    C20H32O11N10
  • C
    C20H40O10N10
  • D
    C20H68O29N10
  • E
    C20H42O12N10

Answer

Correct Answer: C20H32O11N10

Explanation

Introduction:Forming peptide bonds between amino acids is a condensation process that eliminates water. Accounting correctly for the number of water molecules lost is essential for deriving the empirical formula of a peptide from its monomer building blocks.

Given Data / Assumptions:

  • Monomer formula for glycine: C2H5O2N.
  • Ten glycines linked linearly create nine peptide bonds.
  • Each peptide bond formation eliminates one H2O.

Concept / Approach:The total formula is the sum of monomers minus the water molecules removed during condensation. For n residues in a linear chain, there are n − 1 peptide bonds and thus n − 1 waters lost.

Step-by-Step Solution:

Compute monomer sum: 10 * C2H5O2N = C20H50O20N10.Count peptide bonds: 10 residues → 9 bonds → 9 waters removed.Account for water loss: 9 * H2O = H18O9 removed.Subtract: H50 − 18 = H32; O20 − 9 = O11; C and N unchanged.Resulting formula: C20H32O11N10.

Verification / Alternative check:General formula check: for n glycines, overall becomes C(2n) H(5n − 2(n − 1)) O(2n − (n − 1)) N(n) which simplifies to C(2n) H(3n + 2) O(n + 1) N(n). For n = 10, this yields C20H32O11N10, confirming the calculation.

Why Other Options Are Wrong:

  • C20H50O20N10: ignores water loss entirely.
  • C20H40O10N10 and C20H42O12N10: remove the wrong number of hydrogens and oxygens.
  • C20H68O29N10: chemically implausible for a condensation product.

Common Pitfalls:Forgetting that the number of waters lost equals n − 1 for a linear chain, or mistakenly subtracting one water per residue.

Final Answer:C20H32O11N10

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